Ethylamine hydrochloride → 1-benzyl-N-ethylpiperidin-4-amine

HRID 458950Notes

Reaction equation

HRID 458950 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:16]([NH2:18])[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C1COCC1.CO>[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:18][CH2:16][CH3:17])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 192201-Benzyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 106088761-benzyl-N-ethylpiperidin-4-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-phenylmethyl-4-piperidone (25.0 g, 132 mmol) in THF (250 mL) was added ethylamine hydrochloride (12.0 g, 147 mol) and methanol (50 mL) and the resulting mixture stirred at room temperature for 10 min. Sodium triacetoxyborohydride (40 g, 189 mmol) was added portionwise and the resulting mixture stirred at room temperature for 1 h. 2M Sodium hydroxide solution (250 mL) was added and the resulting mixture extracted with diethyl ether. The organic extracts were dried (K2CO3) and evaporated to give 1-phenylmethyl-4-ethylaminopiperidine as an oil. This was dissolved in ethanol (500 mL) and concentrated hydrochloric acid (20 mL) was added. The resulting crystals were collected, washed with diethyl ether and dried giving the sub-titled compound as a solid (38 g); NMR: (CDCl3): 1.10 (t, 3H), 1.40 (m, 2H), 1.83 (m, 2H), 2.02 (m, 2H), 2.65 (q, 2H), 2.85 (m, 2H), 3.50 (s, 2H), 3.75 (m, 1H), 7.2–7.4 (m, 5H); MS: 219 (MH+).

Workup

  1. stirringthe resulting mixture stirred at room temperature for 1 h
  2. extractionthe resulting mixture extracted with diethyl ether
  3. dry with materialThe organic extracts were dried (K2CO3)
  4. customevaporated

Sources & evidence

ORD record
ord-4f3b3ad84fd142ea9df8ca8c9f17e765
Source dataset
uspto-grants-2007_03
Patent number
US07192973B2

Reaction notes

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