1-(Diphenylmethyl)-3-[(2-nitrophenylmethyl)amino]-azetidine → 3-[(2-Aminophenylmethyl)amino]-1-(diphenylmethyl)-azetidine

HRID 1766182Notes

Reaction equation

HRID 1766182 reaction equation
[C:1]1([CH:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:8]2[CH2:11][CH:10]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N+:20]([O-])=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Rh].C>[NH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][CH:10]1[CH2:9][N:8]([CH:7]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11]1

Participants

4

Reactant 1

HCID 211099031-(Diphenylmethyl)-3-[(2-nitrophenylmethyl)amino]-azetidine

Product 1

HCID 211099093-[(2-Aminophenylmethyl)amino]-1-(diphenylmethyl)-azetidine

Reagents, catalysts & solvents 2

HCID 10080373Rhodium carbonCatalystHCID 887MethanolSolvent

Procedure

A solution of 20.0 g (0.5355 mol) of 1-(diphenylmethyl)-3-[(2-nitrophenylmethyl)amino]-azetidine in 200 ml of methanol was hydrogenated in the presence of 4 g of 5% rhodium/charcoal for 5 hours at ambient temperature. The catalyst was filtered off, the filtrate was concentrated by evaporation in vacuo. 17.7 g (96% of theoretical) of a colourless, highly viscous oil were obtained, which was further processed without any additional purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated by evaporation in vacuo
  3. custom17.7 g (96% of theoretical) of a colourless, highly viscous oil were obtained
  4. customwhich was further processed without any additional purification

Sources & evidence

ORD record
ord-734891da2bc948f3b1ba69c827e3506a
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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