Triethylamine → HCID 70850946, compound

HRID 64233Notes

Reaction equation

HRID 64233 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](Cl)=[O:10])=[CH:4][CH:3]=1.[C:12]([C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[C:18]([NH2:21])([CH3:20])[CH3:19])(=[O:14])[CH3:13].C(N(CC)CC)C>ClCCl>[C:12]([C:15]1[CH:16]=[C:17]([C:18]([NH:21][C:9](=[O:10])[CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([CH3:20])[CH3:19])[CH:22]=[CH:23][CH:24]=1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 906924-Chlorophenylacetyl chlorideHCID 698237233-Acetyl-alpha,alpha-dimethylbenzylamine

Product 1

HCID 70850946HCID 70850946, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

4-Chlorophenylacetylchloride (106 mg, 0.56 mmol) in dichloromethane was added to a solution of 3-acetyl-α, α-dimethylbenzylamine 24 (100 mg, 0.56 mmol) and triethylamine (120 μL, 0.86 mmol) in dichloromethane over a period of 5 to 10 min at 0° C. The reaction mixture was stirred at room temperature for 2 h. The mixture was diluted with dichloromethane (20 mL) and washed with 1 N HCl, water and brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by column chromatography using hexane/ethyl acetate as eluent to give 26 (146 mg, 80%). 1H NMR (CDCl3, 400 MHz) δ 1.61 (s, 6H), 2.53 (s, 3H), 3.46 (s, 2H), 5.68 (s, 1H), 7.19 (d, J=7.2 Hz, 2H), 7.30-7.38 (m, 3H), 7.46 (d, J=8 Hz, 1H), 7.75 (d, J=7.2 Hz, 1H), 7.87 (s, 1H); 13C NMR (DMSO-d6 100 MHz) δ 27.26, 29.89, 42.54, 55.34, 124.71, 126.76, 128.74, 128.98, 130.23, 131.45, 131.63, 136.22, 137.19, 148.96, 169.54, 198.59; ESI-HRMS for C19H21NO2Cl (M+H)+ calcd. 330.1261. found 330.1270.

Workup

  1. washwashed with 1 N HCl, water and brine
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f529bde0bbae41d09bae1f567b6a81d5
Source dataset
uspto-grants-2016_09
Patent number
US09447134B2

Reaction notes

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