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

HRID 382660Notes

Reaction equation

HRID 382660 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>[NH2:16][CH2:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][C:7]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9]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, 1.0 equiv) 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 equiv) 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 3 times with CH2Cl2, dried over 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 3 times with CH2Cl2
  3. dry with materialdried over 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-18187e0c32c240f2909c142b14444599
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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