Triethylamine → N-[3-(3,4-bis(trifluoromethyl)benzyloxy)-2-phenylpropyl]-4-fluorobenzamide

HRID 548203Notes

Reaction equation

HRID 548203 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[F:12][C:13]([F:37])([F:36])[C:14]1[CH:15]=[C:16]([CH:29]=[C:30](C(F)(F)F)[CH:31]=1)[CH2:17][O:18][CH2:19][CH:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:21][NH2:22].C(N(CC)CC)C>C(Cl)Cl>[F:36][C:13]([F:37])([F:12])[C:14]1[CH:15]=[C:16]([CH:29]=[CH:30][C:31]=1[C:13]([F:37])([F:36])[F:12])[CH2:17][O:18][CH2:19][CH:20]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:21][NH:22][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 866240403-(3,5-Bis(trifluoromethyl)benzyloxy)-2-phenylpropylamine hydrochloride

Product 1

HCID 86624052N-[3-(3,4-bis(trifluoromethyl)benzyloxy)-2-phenylpropyl]-4-fluorobenzamideYield 188.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-fluorobenzoyl chloride (1.2 mL, 10 mmol) in CH2Cl2 (20 mL) was dropped into a solution of the compound produced in Example 17 (3.31 g, 8.0 mmol) and triethylamine (2.8 mL, 20 mmol) in CH2Cl2 (50 mL) during 30 minutes under cooling with ice. After the solvent was evaporated therefrom in vacuo, water was added to the residue and the mixture was extracted with ethyl acetate. The organic layers were combined, washed with water and a saturated saline solution and dried over anhydrous sodium sulfate. The residual oily product produced by evaporation of the solvent therefrom in vacuo was crystallized from petroleum ether to give the Compound 57 (3.76 g, 94%).

Workup

  1. temperatureunder cooling with ice
  2. customAfter the solvent was evaporated
  3. additionin vacuo, water was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materiala saturated saline solution and dried over anhydrous sodium sulfate
  7. customThe residual oily product produced by evaporation of the solvent
  8. customin vacuo was crystallized from petroleum ether

Sources & evidence

ORD record
ord-302690a9682642b394ab6888491b5004
Source dataset
uspto-grants-2011_05
Patent number
US07939552B2

Reaction notes

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