Hydrochloric Acid → 1-[(Cyclohex-1-en-1-yl)methyl]piperidin-4-amine

HRID 446011Notes

Reaction equation

HRID 446011 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14]C(=O)OC(C)(C)C)[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.Cl.[OH-].[Na+]>CO>[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71293652tert-Butyl N-[1-(cyclohex-1-en-1-ylmethyl)piperidin-4-yl]carbamate

Product 1

HCID 866782451-[(Cyclohex-1-en-1-yl)methyl]piperidin-4-amineYield 95.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tert-butyl N-[1-(cyclohex-1-en-1-ylmethyl)piperidin-4-yl]carbamate obtained in Example 4a (7.47 g, 25.4 mmol), a 5 N aqueous hydrochloric acid solution (25 ml, 125 mmol) and methanol (100 ml) was stirred at 70° C. for 1.5 hours. The reaction mixture was ice-cooled, a 5 N aqueous sodium hydroxide solution (25 ml, 125 mmol) was added, and the solvent was distilled off. Water was added to the residue, which was extracted with ethyl acetate twice. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled off to give the title compound (4.73 g, yield: 95.8%).

Workup

  1. temperaturecooled
  2. distillationthe solvent was distilled off
  3. additionWater was added to the residue, which
  4. extractionwas extracted with ethyl acetate twice
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-6f09c634598749af8bcb0300466c69f2
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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