Cyclopropylamine → 2-Methylpentane

HRID 2233390Notes

Reaction equation

HRID 2233390 reaction equation
[Cl:1][C:2]1[C:3]([C:23]([N:25]2C=CN=[CH:26]2)=[O:24])=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.[CH:30]1(N)C[CH2:31]1>>[CH3:20][CH2:21][CH2:2][CH:3]([CH3:23])[CH3:4].[Cl:1][C:2]1[C:3]([C:23]([NH:25][CH:26]2[CH2:31][CH2:30]2)=[O:24])=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 68580316HCID 68580316, compound

Product 2

HCID 78922-MethylpentaneHCID 59295998HCID 59295998, compound

Procedure

A solution of tert-butyl 4-[3,4-dichloro-2-(1H-imidazol-1-ylcarbonyl)phenoxy]piperidine-1-carboxylate (described in Preparation 11 step 1) (2.0 g, 4.5 mmol) in cyclopropylamine (12 ml) was heated at 50° C. for 14 h. The solution was concentrated in vacuo then partitioned between ethyl acetate and 1N aqueous hydrochloric acid. The organics were dried over magnesium sulfate and concentrated in vacuo. Crystallization from dichloromethane:isohexane gave the title compound as a white solid (0.64 g).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthen partitioned between ethyl acetate and 1N aqueous hydrochloric acid
  3. dry with materialThe organics were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customCrystallization from dichloromethane

Sources & evidence

ORD record
ord-fcd0fcb5ddb04983b429d9cc413d79d5
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

Loading…