Triethylamine → n-(4-Bromobutyl)-dihydro-2-naphtylcarboxamide

HRID 254276Notes

Reaction equation

HRID 254276 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]1[C:11]([OH:13])=O.C(Cl)(=O)C(Cl)=O.[NH2:20][CH:21](O)[CH2:22][CH2:23][CH3:24].C(N(CC)CC)C.C(Br)(Br)(Br)[Br:34].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.C(Cl)Cl.CC#N.CCOC(C)=O>[Br:34][CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:11]([CH:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)=[O:13]

Participants

11

Reactant 6

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 65578Oxalyl chlorideHCID 1030061,2-Dihydro-2-naphthoateHCID 125982441-Aminobutan-1-ol

Product 1

HCID 66852491n-(4-Bromobutyl)-dihydro-2-naphtylcarboxamideYield 64%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the acid (A1) (226 mg, 1.3 mmol), oxalyl chloride (0.14 mL, 1.56 mmol) and two drops of DMF was stirred at room temperature in CH2Cl2 (20 mL) for 2 h. The solvent was evaporated and the residue was used in the next step. To a mixture of aminobutanol (0.13 mL, 1.43 mmol) and triethylamine (0.54 mL, 3.9 mmol) in CH2Cl2 (5 mL) was added a solution of the acid chloride (1.3 mmol) in CH2Cl2 (2 mL). After 12 h the solvent was evaporated and the residue taken in AcOEt (10 mL) washed with H2O, dried and concentrated. The residual solid D1 (300 mg, 90%) was used in the next step. A solution of the hydroxy adduct (300 mg, 1.22 mmol) in CH3CN (10 mL) was cooled at 0° C., and CBr4 (606 mg, 1.83 mmol) and PPh3 (480 mg, 1.83 mmol) were added. After 12 h stirring AcOEt (50 mL) was added and the organic layer was washed with NaOH (20 ml, 1 N), dried and concentrated in vacuo to give the title compound E1 as a solid (240 mg, 64%) after purification by chromatography. 1H NMR (CDCl3 200 MHz): δ 1.70-2.02 (m, 4H), 2.55-260 (m, 2H), 2.86-2.92 (m, 2H), 3.42-3.49 (m, 4H), 5.99 (s, 1H), 7.15-7.27 (m, 4H).

Workup

  1. customThe solvent was evaporated
  2. customAfter 12 h the solvent was evaporated
  3. washwashed with H2O
  4. customdried
  5. concentrationconcentrated
  6. additionwas added
  7. washthe organic layer was washed with NaOH (20 ml, 1 N)
  8. customdried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb18df4ac9cf4e63b9911405d23a714d
Source dataset
uspto-grants-2011_01
Patent number
US07875617B2

Reaction notes

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