Cyclopropanemethanol → HCID 15676949, compound

HRID 1090692Notes

Reaction equation

HRID 1090692 reaction equation
N1C=CN=C1[C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=[O:7].[CH:22]1([CH2:25][OH:26])[CH2:24][CH2:23]1>O1CCOCC1>[C:16]1([CH2:15][N:12]2[CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:26][CH2:25][CH:22]3[CH2:24][CH2:23]3)[CH2:14][CH2:13]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 75644CyclopropanemethanolHCID 21695707HCID 21695707, compound

Product 1

HCID 15676949HCID 15676949, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-imidazolylcarbonylamino-1-phenylmethylpiperidine (10 g, 0.035 mol), from Preparation 2, in dioxane (100 mL) was added to cyclopropanemethanol (2.42 g, 0.035 mol), then heated overnight at 80°-100° C. with stirring. The reaction mixture was allowed to return to room temperature and the dioxane evaporated under reduced pressure, and the residue was flash-chromatographed using ethyl acetate/heptane (50:50) as eluent. 9.5 g of cyclopropylmethyl (1-phenylmethyl-4-piperidyl)carbamate, m.p. 70°-72° C., was recovered and used in the next step without further purification.

Workup

  1. temperatureheated overnight at 80°-100° C.
  2. customto return to room temperature
  3. customthe dioxane evaporated under reduced pressure
  4. customthe residue was flash-chromatographed
  5. custom9.5 g of cyclopropylmethyl (1-phenylmethyl-4-piperidyl)carbamate, m.p. 70°-72° C., was recovered
  6. customused in the next step without further purification

Sources & evidence

ORD record
ord-b3e4029934604fe795522f14bb7a1c17
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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