Acetic Acid → (2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-N-diphenylmethyl-4-piperidinamine

HRID 264703

Reaction equation

HRID 264703 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH:12]([NH2:14])[CH2:11][CH2:10][N:9]1[C:15](=[O:24])[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([BH3-])#N.[Na+].C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH:14][CH:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:11][CH2:10][N:9]1[C:15](=[O:24])[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3102BenzophenoneHCID 5003444Sodium cyanoborohydrideHCID 212202012-Benzyl-1-(3,5-dichlorobenzoyl)-4-piperidinamine

Product 1

HCID 57170253(2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-N-diphenylmethyl-4-piperidinamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 200 mg (0.551 mmol) of (2R*,45*)-2-benzyl-1-(3,5-dichlorobenzoyl)-4-piperidinamine and 110 mg (0.606 mmol) of benzophenone in 5 ml of toluene are kept at reflux for 18 hours. The reaction mixture is then concentrated in a rotary evaporator and dissolved in 3 ml of methanol, and 69 mg (1.10 mmol) of sodium cyanoborohydride are added at RT. The reaction mixture is adjusted to pH=5 with 80 μl of acetic acid and stirred at RT for 68 hours. The title compound ##STR98## is obtained as white foam (120 mg, 41%). TLC:toluene/ethyl acetate (7:3) Rf =0.79, FD-MS:M+ =528, 530; IR:1630 cm-1.

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationThe reaction mixture is then concentrated in a rotary evaporator
  3. dissolutiondissolved in 3 ml of methanol

Sources & evidence

ORD record
ord-ffd66f18dc844192b04fcf55fc735a75
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Linked notes

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