1-Benzyl-4-piperidylamine → N-(2-nitrophenethyl)-1-benzylpiperidin-4-amine

HRID 2378931Notes

Reaction equation

HRID 2378931 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11].[NH2:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15]1>>[N+:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][CH2:2][NH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15]1)([O-:12])=[O:11]

Participants

3

Reactant 2

HCID 4158521-Benzyl-4-piperidylamineHCID 123638782-Nitrophenethyl bromide

Product 1

HCID 16202487N-(2-nitrophenethyl)-1-benzylpiperidin-4-amineYield 81%

Conditions

Temperature
100 °C

Procedure

1-(2-Bromoethyl)-2-nitrobenzene (1.5 g, 6.52 mmol) and 4-amino-1-benzylpiperidine (3.0 ml, 14.71 mmol) were combined. Mixture was heated neat at 100° C. and held with stirring for 17 hours. Mixture was cooled to room temperature. Residue was triturated in 30 mL diethyl ether. Solids were filtered off, washed with diethyl ether and discarded. Filtrate was concentrated. Silica gel chromatography on the residue eluting 2M ammonia in methanol-dichloromethane afforded the title compound as brown oil in 81% yield. MS (M+H)+=340.4.

Workup

  1. temperatureMixture was cooled to room temperature
  2. customResidue was triturated in 30 mL diethyl ether
  3. filtrationSolids were filtered off
  4. washwashed with diethyl ether
  5. concentrationFiltrate was concentrated
  6. washSilica gel chromatography on the residue eluting 2M ammonia in methanol-dichloromethane

Sources & evidence

ORD record
ord-2bb46510d6104a88951902a499dc8a15
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

Loading…