Benzaldehyde → HCID 23509675, compound

HRID 970411Notes

Reaction equation

HRID 970411 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-3d89e6c9a7ca4b30a3847a2762a875eb
Source dataset
uspto-grants-2007_12
Patent number
US07312222B2

Reaction notes

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