N-(4-((oxiran-2-yl)methoxy)phenyl)acetamide → 1-[3-(p-Acetamido-phenoxy)-2-hydroxypropyl]-4-(2-oxo-hexahydro-1-pyrimidinyl)piperidine
Reaction equation
[C:1]([NH:4][C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][CH:11]2[O:13][CH2:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[NH:16]1[CH2:21][CH2:20][CH:19]([N:22]2[CH2:27][CH2:26][CH2:25][NH:24][C:23]2=[O:28])[CH2:18][CH2:17]1>C(O)C>[C:1]([NH:4][C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][CH:11]([OH:13])[CH2:12][N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[CH2:27][CH2:26][CH2:25][NH:24][C:23]3=[O:28])[CH2:18][CH2:17]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]Participants
4
Procedure
A solution of 19.35 g of 1-(p-acetamido-phenoxy)-2,3-epoxy-propane and 9.15 g of 1-(4-piperidyl)-2-oxo-hexahydropyrimidine in 10 ml of abs. ethanol is heated to 95° C. The reaction product crystallises out at boiling heat after about 5 minutes. The crystal broth is diluted with 10 ml of abs. ethanol and heated for a further 5 hours. When the reaction is terminated the batch is evaporated in vacuo and the residue is recrystallised from abs. ethanol/ether to yield the 1-[3-(p-acetamido-phenoxy)-2-hydroxypropyl]-4-(2-oxo-hexahydro-1-pyrimidinyl)-piperidine, which melts at 218°-221° C.
Workup
- customThe reaction product crystallises out
- temperatureat boiling heat after about 5 minutes
- additionThe crystal broth is diluted with 10 ml of abs
- temperatureethanol and heated for a further 5 hours
- customWhen the reaction is terminated the batch
- customis evaporated in vacuo
- customthe residue is recrystallised from abs
Sources & evidence
- ORD record
- ord-cac0f19e89d84616a9e5e2d800025f67
- Source dataset
- uspto-grants-1978_02
- Patent number
- US04075335
Reaction notes
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