Methanol → 2-amino-N-{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-4-fluorobenzamide dihydrochloride

HRID 437645Notes

Reaction equation

HRID 437645 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:29])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[N+:25]([O-])=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CO.[H][H]>[Ni].O1CCCC1>[ClH:1].[ClH:1].[NH2:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[C:17]([NH:16][CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([OH:29])[CH2:9][CH2:10]1)=[O:28]

Participants

6

Reactant 3

HCID 887MethanolHCID 21428896N--{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-4-fluoro-2-nitrobenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 214288302-amino-N-{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-4-fluorobenzamide dihydrochloride

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4.5 parts of N--{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-4-fluoro-2-nitrobenzamide, 40 parts of methanol and 90 parts of tetrahydrofuran is hydrogenated at normal pressure and at room temperature with 2 parts of Raney-nickel catalyst. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is converted into the hydrochloride salt in 2-propanol. The salt is filtered off and dried, yielding 2 parts of 2-amino-N-{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-4-fluorobenzamide dihydrochloride; mp. 210.7° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. filtrationThe salt is filtered off
  4. customdried

Sources & evidence

ORD record
ord-3124d522898b482999353b5a60dd6956
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

Loading…