Water → HCID 69065334, compound

HRID 2109993Notes

Reaction equation

HRID 2109993 reaction equation
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[N+:27]([C:30]1[C:38]2[N:37]=[C:36]([NH:39][CH2:40][CH:41]3[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]3)[NH:35][C:34]=2[CH:33]=[CH:32][CH:31]=1)([O-:29])=[O:28].O>CN(C)C=O.C(O)(=O)C.ClCCl>[C:1]1([CH2:11][N:44]2[CH2:45][CH2:46][CH:41]([CH2:40][NH:39][C:36]3[NH:35][C:34]4[CH:33]=[CH:32][CH:31]=[C:30]([N+:27]([O-:29])=[O:28])[C:38]=4[N:37]=3)[CH2:42][CH2:43]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 61951-NaphthaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23068968HCID 23068968, compound

Product 1

HCID 69065334HCID 69065334, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21926011acetic acid N,N-dimethylformamideSolvent

Procedure

After adding 1-naphthoaldehyde (3 mmol) and sodium triacetoxyborohydride (3 mmol) to a solution of (4-nitro-1H-benzimidazol-2-yl)-piperidin-4-ylmethyl-amine (450 mg, 1 mmol) in dimethylformamide-acetic acid (10:1) (7 mL), the mixture was stirred at room temperature overnight. Water and dichloromethane were added, and extraction was performed with dichloromethane. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/triethylamine=100/0→98/2) to obtain (1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-(4-nitro-1H-benzimidazol-2-yl)-amine. The compound was identified by LC-MS.

Workup

  1. extractionextraction
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/triethylamine=100/0→98/2)

Sources & evidence

ORD record
ord-59d1e501795e4bdd8c56845370a6d0e9
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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