Acetic Acid → 1-benzyl-N,4-dimethylpiperidin-3-amine

HRID 458651Notes

Reaction equation

HRID 458651 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]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 6329MethylamineHCID 8028Tetrahydrofuran

Product 1

HCID 99438891-benzyl-N,4-dimethylpiperidin-3-amineYield 87.75%

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

  1. stirringthe new mixture stirred at room temperature for 18 hours
  2. customThe reaction was quenched with 2 N hydrochloric acid
  3. washThe reaction mixture was washed two times with ether
  4. extractionextracted three times with dichloromethane The combined dichloromethane layers
  5. dry with materialwere dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-99da70a9dcf64445b519911709629c89
Source dataset
uspto-grants-2007_03
Patent number
US07192963B2

Reaction notes

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