Benzaldehyde → HCID 23509675, compound

HRID 2270096Notes

Reaction equation

HRID 2270096 reaction equation
Cl.Cl.[C:3]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][NH:17][CH:16]([CH2:20][N:21]3[CH2:26][CH2:25][CH:24]([CH2:27][C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH2:23][CH2:22]3)[CH2:15]2)=[O:13])[CH:8]=[CH:9][CH:10]=1)#[N:4].[CH:35](=O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:35]([N:17]1[CH2:18][CH2:19][N:14]([C:12]([NH:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:3]#[N:4])[CH:6]=2)=[O:13])[CH2:15][CH:16]1[CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)[CH2:23][CH2:22]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23509691HCID 23509691, compound

Product 1

HCID 23509675HCID 23509675, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of N-(3-cyanophenyl)-3-{[4-(4-fluorobenzyl)-1-piperidinyl]methyl}-1-piperazinecarboxamide dihydrochloride (20.0 mg, 0.05 mmol) and benzaldhyde (8.5 mg, 0.08 mmol, Aldrich) in dry dichloroethane (5 mL) was stirred for 20 min when sodium triacetoxyborohydride (32 mg, 0.15 mmol, Aldrich) was added. The reaction was stirred for 16 h and then quenched with water (5 mL). The organic layer was separated, dried over MgSO4, and conc. in vacuo to a white solid. The solid was purified by flash chromatography (SiO2, EtOAc and then EtOAc:TEA, 9:1) to yield 5.0 mg of 4-benzyl-N-(3-cyanophenyl)-3-{[4-(4-fluorobenzyl)-1-piperidinyl]methyl}-1-piperazinecarboxamide as a white solid. MS (ESI) 526 (M+H).

Workup

  1. additionwas added
  2. customquenched with water (5 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. customThe solid was purified by flash chromatography (SiO2, EtOAc

Sources & evidence

ORD record
ord-e71832a1fc744fe4ae0d19e852e8dfdd
Source dataset
uspto-grants-2001_12
Patent number
US06331545B1

Reaction notes

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