Sodium triacetoxyborohydride → 2-Methyl-5-{4-[2-(3-nitrophenyl)propyl]-1-piperazinyl}quinoline

HRID 734566Notes

Reaction equation

HRID 734566 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([CH3:13])[CH:11]=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N:25]2[CH2:30][CH2:29][N:28](CCC3C=C(C=CC=3)N)[CH2:27][CH2:26]2)[N:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N:25]2[CH2:30][CH2:29][N:28]([CH2:11][CH:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[CH3:13])[CH2:27][CH2:26]2)[N:16]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 226741372-(3-Nitrophenyl)propanalHCID 498521053-(2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}aniline

Product 1

HCID 574443342-Methyl-5-{4-[2-(3-nitrophenyl)propyl]-1-piperazinyl}quinolineYield 133.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(3-nitrophenyl)propanal (1.2 equiv. 50 mg), 2-methyl-5-(1-piperazinyl)quinoline (D3) (52 mg) and DCM (2 mL) was stirred for 1 h. Sodium triacetoxyborohydride (1.2 equiv., 58 mg) was added and the resulting mixture was stirred for 18 h. The reaction mixture was concentrated in vacuo and purified using ion-exchange chromatography (SCX-2), eluting with methanol followed by ammonia in methanol (1M). The basic fractions were concentrated under vacuum and purified by chromatography (SPE, SiO2) using DCM-methanol (98:2) as eluent to afford the title compound as yellow liquid (78 mg, 78% yield).

Workup

  1. stirringthe resulting mixture was stirred for 18 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified
  4. washeluting with methanol
  5. concentrationThe basic fractions were concentrated under vacuum
  6. custompurified by chromatography (SPE, SiO2)

Sources & evidence

ORD record
ord-6e5956d0f72c47769561f21251436165
Source dataset
uspto-grants-2009_09
Patent number
US07592346B2

Reaction notes

Loading…