1-Benzyl-N-(2-nitrophenyl)piperidin-4-amine → N1-(1-benzylpiperidin-4-yl)benzene-1,2-diamine

HRID 437657Notes

Reaction equation

HRID 437657 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)([O-])=O.[H][H]>[Ni].O1CCCC1>[C:18]1([CH2:17][N:14]2[CH2:15][CH2:16][CH:11]([NH:10][C:5]3[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:12][CH2:13]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 816751-Benzyl-N-(2-nitrophenyl)piperidin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 93779N1-(1-benzylpiperidin-4-yl)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 31 parts of N-(2-nitrophenyl)-1-(phenylmethyl)-4-piperidinamine in 160 parts of tetrahydrofuran is hydrogenated at normal pressure and at a temperature of 40° C, with 20 parts of Raney nickel catalyst. After the calculated amount of hydrogen is taken up (3 moles) hydrogenation is stopped. The catalyst is filtered off and from the filtrate the solvent is evaporated. The solid residue is washed with 160 parts of 2,2'-oxybispropane, to yield 22 parts of N-[1-(phenylmethyl)-4-piperidinyl]-1,2-benzenediamine; mp. 112°-113° C. On concentrating the filtrate to about one quarter of its volume a second crop of 2.5 parts of N-[1-(phenylmethyl)-4-piperidinyl]-1,2-benzenediamine is obtained; mp. 108°-109° C.

Workup

  1. filtrationThe catalyst is filtered off and from the filtrate the solvent
  2. customis evaporated
  3. washThe solid residue is washed with 160 parts of 2,2'-oxybispropane

Sources & evidence

ORD record
ord-ddd0e36b20eb4268a92c4ef6cee40dd9
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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