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

HRID 616598Notes

Reaction equation

HRID 616598 reaction equation
[CH2:1]([O:4][C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH2:8][CH:9]1[O:11][CH2:10]1)[CH:2]=[CH2:3].[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>[CH2:1]([O:4][C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH2:8][CH:9]([OH:11])[CH2:10][N: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)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 5743337[[o-(Allyloxy)phenoxy]methyl]oxiraneHCID 155726661-(Piperidin-4-yl)-1,3-diazinan-2-one

Product 1

HCID 203680361-[3-(o-Allyloxy-phenoxy)-2-hydroxypropyl]-4-(2-oxo-hexahydro-1-pyrimidinyl)piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10.3 g of 1-(o-allyloxy-phenoxy)-2,3-epoxy-propane and 9.15 g of 1-(4-piperidyl)-2-oxo-hexahydropyrimidine in 7 ml abs. ethanol is heated for 5 hours to 95° C and then evaporated in vacuo. The residue is recrystallised from isopropanol to yield the 1-[3-(o-allyloxy-phenoxy)-2-hydroxypropyl]-4-(2-oxo-hexahydro-1-pyrimidinyl)-piperidine, which melts at 122°-125° C.

Workup

  1. customevaporated in vacuo
  2. customThe residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-78a02935df9f4be98813576cff7f00fe
Source dataset
uspto-grants-1978_02
Patent number
US04075208

Reaction notes

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