Hydrochloric Acid → 3-Amino-propyl-4,4-diphenyl piperidine

HRID 1275224Notes

Reaction equation

HRID 1275224 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]#[N:16])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[OH-].[Na+]>C1COCC1>[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][NH2:16])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 155128643-(4,4-Diphenylpiperidin-1-yl)propionitrile

Product 1

HCID 101085183-Amino-propyl-4,4-diphenyl piperidineYield 66.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-(4,4-diphenylpiperidin-1-yl)propionitrile (2.00 g, 6.89 mmol) in anhydrous THF (20 mL) under argon was added a solution of BH3 in THF (1.0 M, 24.1 mL, 24 mmol, 3.5 eq) at room temperature. The mixture was refluxed for 4.5 hours and then cooled to room temperature. Aqueous HCl (6 N, 50 mL) was added and stirring was continued for 1 hour. The mixture was basified to pH 9 by addition of 6 N aq. NaOH, extracted with CH2CL2 (3×10 mL), dried (MgSO4) and concentrated. The residue was purified by flash chromatography (SiO2, EtOAc-MeOH-isopropylamine 9:1:0 to 4:1:0.2) to give 1.35 g (66%) of tan solid, which was characterized spectroscopically.

Workup

  1. temperatureThe mixture was refluxed for 4.5 hours
  2. extractionextracted with CH2CL2 (3×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (SiO2, EtOAc-MeOH-isopropylamine 9:1:0 to 4:1:0.2)

Sources & evidence

ORD record
ord-a2b03a3615f44884a83fcb2276a5dec6
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

Loading…