Triethylamine → HCID 18638022, compound

HRID 1165388Notes

Reaction equation

HRID 1165388 reaction equation
[CH2:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].C(Cl)(=O)C(Cl)=O.[C:20]1([C@@H:30]([NH2:32])[CH3:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>CN(C)C=O.C(Cl)Cl>[C:20]1([C@@H:30]([NH:32][C:9](=[O:11])[C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[CH:13][CH:12]=2)[CH3:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 663251-Naphthalenemethanamine, alpha-methyl-, (alphaS)-HCID 4606904-(Prop-2-en-1-yloxy)benzoic acid

Product 1

HCID 18638022HCID 18638022, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4-Allyloxybenzoic acid (2.0 g, 0.011 mole) was stirred in a mixture of 3 equivalents of oxalyl chloride, 25 mL of anhydrous methylene chloride and one drop of dimethylformamide (DMF) at room temperature for 2 hours. The solvent and excess oxalyl chloride were removed under vacuum. Benzene (10 mL) was added and the material was again subjected to vacuum distillation to remove the remaining traces of oxalyl chloride. The remaining light yellow oil was dissolved in 25 mL of anhydrous methylene chloride, and the resulting solution was added dropwise to an ice cold, stirring solution of 2 g (0.012 mole) of (S)-1-(1-naphthyl)ethylamine (Aldrich) and 1 equivalent of triethylamine in 50 mL of anhydrous methylene chloride. The mixture was stirred at 0° C. for 2 h and at room temperature for 1 h. The resulting methylene chloride solution was washed successively with 0.1N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution, and then with water. The phases were separated, and the aqueous phase was extracted twice with 50 mL portions of methylene chloride. The methylene chloride phases were combined, dried over anhydrous magnesium sulfate, and the solvent was removed to give (S)-N-1-(1-naphthyl)ethyl-4-allyloxybenzamide as a crude solid. The solid was recrystallized from absolute ethanol to give white crystals, 2.25 g (62%); mp 141°-143° C.; [α]D25 +58.18° (c=0.373, CHCl3); IR (KBr): 3220 and 1625 cm-1 ; NMR (δ): 1.80 (3H, d, J=7.5 Hz), 4.56 (2H, d, J=5 Hz), 5.24-5.56 (2H, m,), 5.86-6.20 (2H, m), 6,36 (1H, q, J=6 Hz), 6.80-7.00 (2H, m); 7.40-8.28 (9H, m). Anal. for C22H21NO2 : Calcd: C, 79.75; H, 6.34, N, 4.22. Found: C, 79.62; H, 6.40; N, 4.44.

Workup

  1. customThe solvent and excess oxalyl chloride were removed under vacuum
  2. additionBenzene (10 mL) was added
  3. distillationthe material was again subjected to vacuum distillation
  4. customto remove the remaining traces of oxalyl chloride
  5. dissolutionThe remaining light yellow oil was dissolved in 25 mL of anhydrous methylene chloride
  6. additionthe resulting solution was added dropwise to an ice cold
  7. washThe resulting methylene chloride solution was washed successively with 0.1N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution
  8. customThe phases were separated
  9. extractionthe aqueous phase was extracted twice with 50 mL portions of methylene chloride
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was removed

Sources & evidence

ORD record
ord-cc9e9729b0bc4345b1e174a23b519a29
Source dataset
uspto-grants-1990_03
Patent number
US04909935

Reaction notes

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