Acetic Acid → (1-Benzylpiperidin-4-yl)-[2-(5-methoxy-2-nitrophenyl)-ethyl]-amine

HRID 2059970Notes

Reaction equation

HRID 2059970 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH2:9][CH2:10][NH2:11])[CH:8]=1.[CH2:15]([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C:23]1=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH2:15]([N:22]1[CH2:27][CH2:26][CH:25]([NH:11][CH2:10][CH2:9][C:7]2[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[N+:12]([O-:14])=[O:13])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 51700761-Benzyl-2-piperidoneHCID 186219752-(5-Methoxy-2-nitrophenyl)ethan-1-amine

Product 1

HCID 21109931(1-Benzylpiperidin-4-yl)-[2-(5-methoxy-2-nitrophenyl)-ethyl]-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere a mixture of 9.98 g (50.9 mmol) 2-(5-methoxy-2-nitrophenyl)-ethylamine, 9.80 mL (54.9 mmol) N-benzylpiperidone and 6.30 mL (114 mmol) acetic acid in 270 mL dichloromethane was cooled to 0° C. in an ice bath. At this temperature 14.2 g (67.0 mmol) sodium triacetoxyborohydride were added batchwise within 20 min. The reaction mixture was left for a further 4 h at 0° C. and warmed up to RT overnight. Then the mixture was combined with 400 mL of a 15% (w/v) aqueous potassium carbonate solution and stirred for 1 h at RT. The organic phase was separated off, dried and concentrated by rotary evaporation.

Workup

  1. temperaturewarmed up to RT overnight
  2. customThe organic phase was separated off
  3. customdried
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-f8d1e6c614d642959df3db15c2d2487a
Source dataset
uspto-grants-2012_10
Patent number
US08278336B2

Reaction notes

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