Triethylamine → 1-cyclohexyl-N-[(1S)-1-(furan-2-yl)ethyl]piperidin-4-amine

HRID 1618114Notes

Reaction equation

HRID 1618114 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C@@H:6]([NH2:8])[CH3:7].[CH:9]1([N:15]2[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C.C([BH3-])#N.[Na+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl.CO>[CH:9]1([N:15]2[CH2:20][CH2:19][CH:18]([NH:8][C@H:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[CH3:7])[CH2:17][CH2:16]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 7047669(1S)-1-(furan-2-yl)ethan-1-amineHCID 122527641-Cyclohexylpiperidin-4-one

Product 1

HCID 671921261-cyclohexyl-N-[(1S)-1-(furan-2-yl)ethyl]piperidin-4-amineYield 52.1%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(1S)-1-(Furan-2-yl)ethanamine (0.55 gr, 5 mmol) and 1-cyclohexylpiperidin-4-one (0.91 gr, 5 mmol) were dissolved in dry dichloromethane (20 mL) in the presence of triethylamine (2 mL, 15 mmol) and titanium(IV) chloride (1M in dichloromethane, 2.5 mmol, 2.5 mL). Reaction mixture was stirred under nitrogen atmosphere for 16 hours. After dilution with methanol (10 mL), sodium cyanoborohydride was added (0.95 gr, 25 mmol) and the resulting reaction mixture was stirred for 4 hours. After dilution with ethyl acetate, the organic phase was washed with 15% ammonium hydroxide and evaporated to dryness. Title compound (0.72 gr, Y=52%) was isolated by column chromatography (dichloromethane/methanol/7N ammonia in methanol 96:2:2)

Workup

  1. customReaction mixture
  2. customthe resulting reaction mixture
  3. stirringwas stirred for 4 hours
  4. washAfter dilution with ethyl acetate, the organic phase was washed with 15% ammonium hydroxide
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-687ca5b695e643df81bb412f7b85e413
Source dataset
uspto-grants-2014_07
Patent number
US08765972B2

Reaction notes

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