Triethylamine → 4-(diphenylmethyl) N-(2-nitrophenyl)-1-piperazinepropanamine hydrochloride

HRID 2050276Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13].[C:15]1([CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>CN(C)C(=O)C>[ClH:1].[C:28]1([CH:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:22]2[CH2:23][CH2:24][N:25]([CH2:2][CH2:3][CH2:4][NH:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N+:12]([O-:14])=[O:13])[CH2:26][CH2:27]2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 21.5 parts of N-(3-chloropropyl)-2-nitrobenzenamine, 22.68 parts of 1-(diphenylmethyl)piperazine, 20 parts of N,N-diethylethanamine and 180 parts of N,N-dimethylacetamide is stirred and heated for 6 hours at 100° C. The reaction mixture is evaporated and the residue is taken up in water. The oily product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is crystallized from a mixture of 2-propanol, ethanol and 2,2'-oxybispropane. The product is filtered off and dried, yielding 4-(diphenylmethyl)-N-(2-nitrophenyl)-1-piperazinepropanamine hydrochloride; mp. 228° C.

Workup

customThe reaction mixture is evaporated
extractionThe oily product is extracted with trichloromethane
customThe extract is dried
filtrationfiltered
customevaporated
customThe residue is crystallized from a mixture of 2-propanol, ethanol and 2,2'-oxybispropane
filtrationThe product is filtered off
customdried

Sources & evidence

ORD record: ord-69d88038452b4aa99fe222c87246e143
Source dataset: uspto-grants-1980_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04200641

Reaction notes

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