Propylene Oxide → HCID 20223068, compound

HRID 979829Notes

Reaction equation

HRID 979829 reaction equation
[C:1]([C:3]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:5][CH2:6][NH:7][CH3:8])#[N:2].[CH2:22]1[O:25][CH:23]1[CH3:24]>CO>[C:1]([C:3]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:5][CH2:6][N:7]([CH2:22][CH:23]([CH3:24])[OH:25])[CH3:8])#[N:2]

Participants

4

Reactant 2

HCID 6378Propylene Oxide2×HCID 93168Verapamil metabolite D617

Product 1

HCID 20223068HCID 20223068, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 18.9 g of 4-cyano-4-(3,4-dimethoxyphenyl)-5,N-dimethyl-hexylamine and 4.5 g of propylene oxide in 40 ml of methanol was allowed to stand for 24 hours at 20° C. A further 0.75 g of propylene oxide was then added, and after 24 hours at 20° C. the solution was refluxed for 1 hour and then evaporated to dryness in vacuo. The oil thus obtained was purified by silica gel chromatography using chloroform containing increasing amounts of methanol as eluent. The unitary TLC fractions (chloroform:methanol:5N methanolic ammonia 95:5:0.5 by volume) were evaporated to dryness to give 18.78 g of the title compound as an oil.

Workup

  1. customevaporated to dryness in vacuo
  2. customThe oil thus obtained
  3. customwas purified by silica gel chromatography
  4. temperatureincreasing amounts of methanol as eluent
  5. customThe unitary TLC fractions (chloroform:methanol:5N methanolic ammonia 95:5:0.5 by volume) were evaporated to dryness

Sources & evidence

ORD record
ord-b0e5cec92d4649d7920544f6ae788d97
Source dataset
uspto-grants-1987_01
Patent number
US04634712

Reaction notes

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