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

HRID 354955Notes

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-0db3de88308c44449ad4960f8921f52f
Source dataset: uspto-grants-1983_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04377578

Reaction notes

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