Triethylamine → Rac-3-chloro-n-({[(4-chloro-phenyl)-phenyl-methyl]-carbamoyl}-methyl)-benzamide

HRID 2425184Notes

Reaction equation

HRID 2425184 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH:6][CH:7]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].C(N(CC)CC)C.[Cl:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32](Cl)=[O:33]>ClCCl>[Cl:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32]([NH:2][CH2:3][C:4](=[O:5])[NH:6][CH:7]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69252Benzoyl chloride, 3-chloro-HCID 672464382-Amino-N-[(4-chloro-phenyl)-phenyl-methyl]-acetamide hydrochloride

Product 1

HCID 59689126Rac-3-chloro-n-({[(4-chloro-phenyl)-phenyl-methyl]-carbamoyl}-methyl)-benzamideYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 0.32 mmol rac-2-amino-N-[(4-chloro-phenyl)-phenyl-methyl]-acetamide hydrochloride (Example 3.1) in 5 ml of dichloromethane was treated with 1.61 mmol of triethylamine. The resulting slurry was cooled to 0° C. and 0.35 mmol of 3-chlorobenzoyl chloride was added. The mixture was stirred for 1 hour at room temperature, concentrated and hydrolysed. The organic phase was dried over magnesium sulfate and concentrated. The residue was triturated with diethyl ether to give the title compound as a colorless solid. Yield=97%.

Workup

  1. concentrationconcentrated
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-18b1c69905004f33b9aa449bb3035c10
Source dataset
uspto-grants-2011_06
Patent number
US07964645B2

Reaction notes

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