Ammonium Chloride → 4-Methyl-1-phenylpent-1-yn-3-amine
Reaction equation
[CH3:1][CH:2]([CH3:19])[CH:3]([N:12]1CCC(=O)CC1)[C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl-].[NH4+]>>[CH3:1][CH:2]([CH3:19])[CH:3]([NH2:12])[C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
3
Conditions
- Temperature
- 90 °C
Procedure
A 25 ml pressure tube was charged with 1-(4-methyl-1-phenylpent-1-yn-3-yl)piperidin-4-one (76.6 mg, 0.30 mmol) and ammonium chloride (48 mg, 0.90 mmol). The pressure tube was purged with argon for 5 min and then saturated ethanolic ammonia solution (2 ml) was added. The pressure tube was sealed tightly and the reaction mixture was stirred at 90° C. for 4 hrs. The reaction mixture was concentrated under reduced pressure and the brown residue was subjected to flash chromatography on silica gel (EtOAc/MeOH=19:1) to give 33.3 mg of a pure title compound as a yellowish oil. (yield: 64%)
Workup
- customThe pressure tube was purged with argon for 5 min
- additionsaturated ethanolic ammonia solution (2 ml) was added
- customThe pressure tube was sealed tightly
- concentrationThe reaction mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f91ebca499ba4e3e976ee331babdcd82
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790882B2
Reaction notes
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