Tetrahydrofuran → 2-amino-N-{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}benzamide dihydrochloride hemihydrate

HRID 437644Notes

Reaction equation

HRID 437644 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:29])[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH:17][C:18](=[O:28])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N+:25]([O-])=[O:26])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.O1CCCC1.[H][H]>CO>[OH2:26].[ClH:2].[ClH:1].[NH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]([NH:17][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][C:9]([C:6]2[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=2)([OH:29])[CH2:10][CH2:11]1)=[O:28].[NH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]([NH:17][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][C:9]([OH:29])([C:6]2[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1)=[O:28].[ClH:2].[ClH:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21428974N-{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-2-nitrobenzamide hydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 1317108222-amino-N-{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}benzamide dihydrochloride hemihydrate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.5 parts of N-{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-2-nitrobenzamide hydrochloride, 90 parts of tetrahydrofuran and 40 parts of methanol is hydrogenerated at normal pressure and at room temperature with 0.2 parts of platinium dioxide. 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 and 2,2'-oxybispropane. The salt is filtered off and dried, yielding 2.6 parts of 2-amino-N-{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}benzamide dihydrochloride hemihydrate; mp. 195.7° 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-4b49f81c3aa9442a80c61ba2679973a1
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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