Acetic Acid → 4'-Trifluoromethylbiphenyl-2-carboxylic acid-(2-phenethyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-amide

HRID 1954428Notes

Reaction equation

HRID 1954428 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[C:30]1([CH2:36][CH:37]=O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.C(Cl)Cl>[CH2:37]([N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=4)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:6]=2)[CH2:1]1)[CH2:36][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 998PhenylacetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 110147584'-Trifluoromethyl-biphenyl-2-carboxylic acid (1,2,3,4tetrahydroisoquinolin-6-yl)-amide

Product 1

HCID 154896134'-Trifluoromethylbiphenyl-2-carboxylic acid-(2-phenethyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-amide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A 400 mg (1.01 mmole) sample of compound (II), phenylacetaldehyde (121 mg, 1.01 mmole), sodium triacetoxyborohydride (320 mg, 1.52 mmole) and acetic acid (61 mg, 1.01 mmole) were stirred in 10 mL of 1,2-dichloroethane for 12 hrs. at ambient temperature. The reaction was diluted with methylene chloride, washed with 1N NaOH, water and brine. Purification was carried out with silica gel chromatography using 50% ethyl acetate/hexanes as the eluent.

Workup

  1. customat ambient temperature
  2. washwashed with 1N NaOH, water and brine
  3. customPurification

Sources & evidence

ORD record
ord-5a12cc7b815041c590e1496982ccc2f8
Source dataset
uspto-grants-2000_09
Patent number
US06121283

Reaction notes

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