Acetic Acid → 1-benzyl-N,4-dimethylpiperidin-3-amine
Reaction equation
[CH3:1][NH2:2].[C:3](O)(=O)[CH3:4].[CH2:7]1[CH2:11]O[CH2:9][CH2:8]1>>[CH2:9]([N:2]1[CH2:4][CH2:3][CH:3]([CH3:4])[CH:9]([NH:2][CH3:1])[CH2:1]1)[C:8]1[CH:11]=[CH:7][CH:8]=[CH:11][CH:7]=1Participants
Procedure
To a stirred solution of the product from Method E (3.81 grams/0.019 mol) and 38 mL of 2.0 M methylamine in THF was added 2.2 mL of acetic acid and the resulting mixture stirred at room temperature for 1.5 hours. Triacetoxysodiumborohydride (NaB(OAc)3H) (7.94 grams/0.038 mol) was added as a solid and the new mixture stirred at room temperature for 18 hours. The reaction was quenched with 2 N hydrochloric acid and the pH adjusted to 1. The reaction mixture was washed two times with ether, the aqueous layer then adjusted to pH of 12 with 6 N sodium hydroxide (aq) and extracted three times with dichloromethane. The combined dichloromethane layers were dried over Na2SO4 filtered and evaporated to dryness in vacuo affording 3.51 grams (87.75%) of the title compound as dark yellow oil. LRMS: 219.1 (M+1).
Workup
- stirringthe new mixture stirred at room temperature for 18 hours
- customThe reaction was quenched with 2 N hydrochloric acid
- washThe reaction mixture was washed two times with ether
- extractionextracted three times with dichloromethane
- dry with materialThe combined dichloromethane layers were dried over Na2SO4
- filtrationfiltered
- customevaporated to dryness in vacuo
Sources & evidence
- ORD record
- ord-fc39828bd31d4e88ad9de314384a60ba
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06962993B2
Reaction notes
Loading…