Dimethylamine, hydrochloride → HCID 22278842, compound

HRID 1865235Notes

Reaction equation

HRID 1865235 reaction equation
C([BH3-])#N.[Na+].C(OC([N:12]1[CH2:17][CH2:16][C:15](=O)[CH:14]([CH2:19][CH3:20])[CH2:13]1)=O)(C)(C)C.Cl.[CH3:22][NH:23][CH3:24].[OH-].[K+]>CO>[CH3:22][N:23]([CH3:24])[CH:15]1[CH2:16][CH2:17][NH:12][CH2:13][CH:14]1[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 22278903tert-Butyl 3-ethyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 22278842HCID 22278842, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (3.2 g, 50.8 mmol) was added to the stirred suspension of N-tert.-butoxycarbonyl-3-ethyl-4-piperidone (8 g, 35 mmol), N,N-dimethylamine hydrochloride (14 g, 172 mmol) and KOH (9.6 g, 172 mmol) in methanol (50 ml) at 0° C. The resulting mixture was stirred for 4 hr at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water, acidified with conc. HCl (pH 3˜4) and extracted with ethyl acetate to remove impurities. The aqueous layer was basified with 1 M sodium hydroxide solution (pH˜10) and extracted with ethyl acetate. Ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to give 4-dimethylamino-3-ethylpiperidine. Yield 2.3 g (37%), C9H20N2, m/z 157 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with water
  3. extractionextracted with ethyl acetate
  4. customto remove impurities
  5. extractionextracted with ethyl acetate
  6. extractionEthyl acetate extract
  7. dry with materialwas dried (Na2SO4)
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a7dc93bfd7fb46eebb2888a7129da56f
Source dataset
uspto-grants-2009_12
Patent number
US07626032B2

Reaction notes

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