Hydrochloric Acid → HCID 19085426, compound
Reaction equation
CN(C[N:5]=[CH:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22]Br)=[CH:16][CH:15]=1.C1(C)C=CC=CC=1.[ClH:31]>CCOCC.C(N(CC)CC)C>[ClH:13].[ClH:31].[NH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][N:10]([CH2:22][CH2:21][O:20][C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=2)[CH2:11][CH2:12]1Participants
Procedure
A mixture of 4-(dimethylaminomethyliminomethyl)piperidine (7.2 g, prepared as in Example 1), 2-bromoethyl 4-chlorophenyl ether (10.0 g), toluene (100 ml) and triethylamine (5.9 ml) was heated on a steam bath for 6 hours. The mixture was evaporated to dryness and the residue was dissolved in a 1:1 mixture of methanol/concentrated aqueous ammonia solution (S.G. 0.880, 80 ml). The mixture was stirred at ambient temperature for 16 hours and then evaporated to dryness. Water (50 ml) was added to the residue and the mixture was extracted with dichloromethane to give an oil. The oil was dissolved in ether and acidified with ethereal hydrogen chloride to give 4-aminomethyl-1-[2-(4-chlorophenoxy)ethyl]piperidine dihydrochloride m.p. 250°-252° C.
Workup
- temperaturewas heated on a steam bath for 6 hours
- customThe mixture was evaporated to dryness
- dissolutionthe residue was dissolved in a 1:1 mixture of methanol/concentrated aqueous ammonia solution (S.G. 0.880, 80 ml)
- customevaporated to dryness
- additionWater (50 ml) was added to the residue
- extractionthe mixture was extracted with dichloromethane
- customto give an oil
Sources & evidence
- ORD record
- ord-ec757cf3dc164686adae9bbfeb3ecd12
- Source dataset
- uspto-grants-1998_06
- Patent number
- US05760035
Reaction notes
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