Triethylamine → N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-3-cyano-benzamide

HRID 2244033Notes

Reaction equation

HRID 2244033 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7])#[N:2].[NH2:12][C:13]1[CH:14]=[C:15]([CH:31]=[CH:32][CH:33]=1)[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[C:20]([OH:27])[C:19]=1[CH2:28][CH2:29][CH3:30].C(N(CC)CC)C>ClCCl>[C:24]([C:21]1[CH:22]=[CH:23][C:18]([O:17][CH2:16][C:15]2[CH:14]=[C:13]([NH:12][C:6](=[O:7])[C:5]3[CH:9]=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=3)[CH:33]=[CH:32][CH:31]=2)=[C:19]([CH2:28][CH2:29][CH3:30])[C:20]=1[OH:27])(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3084833-Cyanobenzoyl chlorideHCID 145235601-{4-[(3-Aminophenyl)methoxy]-2-hydroxy-3-propylphenyl}ethan-1-one

Product 1

HCID 68431147N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-3-cyano-benzamideYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add a solution of 3-cyanobenzoyl chloride (553 mg, 3.34 mmol) in dichloromethane (10 mL) to a solution of 1-[4-(3-amino-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone (1.00 g, 3.34 mmol) in dichloromethane (10 mL), and triethyl amine (1.4 mL) at 0° C. Stir to room temperature for one hour. Partition the mixture between dichloromethane (20 mL) and 2N hydrochloric acid (30 mL). Wash the organic layer with 2N hydrochloric acid (20 mL), saturated sodium bicarbonate, brine, dry, filter, and concentrate to afford the title compound as a light yellow powder (1.33 g, 93%): 1H NMR (CDCl3) δ 0.96 (t, 3H), 1.59 (sextet, 2H), 2.55 (s, 3H), 2.72 (t, 2H), 5.19 (s, 2H), 6.47 (d, 1H), 7.26 (d, 1H), 7.42 (t, 1H), 7.54-7.59 (m, 2H), 7.65 (t, 1H), 7.77 (s, 1H), 7.84 (d, 1H), 7.88 (s, 1H), 8.11 (d, 1H), 8.17 (s, 1H), 12.75 (s, 1H).

Workup

  1. customPartition the mixture between dichloromethane (20 mL) and 2N hydrochloric acid (30 mL)
  2. washWash the organic layer with 2N hydrochloric acid (20 mL), saturated sodium bicarbonate, brine
  3. customdry
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-cd4f9e4934c24032933e782465c8aad1
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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