2-(2-Chlorophenoxymethyl)oxirane → 1-[3-(o-Chloro-phenoxy)-2-hydroxypropyl]-4-(2-oxo-hexahydro-1-pyrimidinyl)-piperidine

HRID 616597

Reaction equation

HRID 616597 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]1[O:8][CH2:7]1.[NH:13]1[CH2:18][CH2:17][CH:16]([N:19]2[CH2:24][CH2:23][CH2:22][NH:21][C:20]2=[O:25])[CH2:15][CH2:14]1>C(O)C>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]([OH:8])[CH2:7][N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[CH2:24][CH2:23][CH2:22][NH:21][C:20]2=[O:25])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 1375002-(2-Chlorophenoxymethyl)oxiraneHCID 155726661-(Piperidin-4-yl)-1,3-diazinan-2-one

Product 1

HCID 203680541-[3-(o-Chloro-phenoxy)-2-hydroxypropyl]-4-(2-oxo-hexahydro-1-pyrimidinyl)-piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 9.2 g of 1-(o-chloro-phenoxy)-2,3-epoxypropane and 9.15 g of 1-(4-piperidyl)-2-oxo-hexahydro-pyrimidine in 7 ml of abs. ethanol is heated for 5 hours to 95° C and then evaporated in vacuo. The residue is recrystallised from chloroform/petroleum ether to yield the 1-[3-(o-chloro-phenoxy)-2-hydroxypropyl]-4-(2-oxo-hexahydro-1-pyrimidinyl)-piperidine, which melts at 150°-153° C.

Workup

  1. customevaporated in vacuo
  2. customThe residue is recrystallised from chloroform/petroleum ether

Sources & evidence

ORD record
ord-60e4d567e76e4e1ab314759720cea9a5
Source dataset
uspto-grants-1978_02
Patent number
US04075208

Linked notes

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