Hydrogen chloride-ethyl acetate → HCID 28305814, compound

HRID 2354099Notes

Reaction equation

HRID 2354099 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][C@@H:12]([NH:16]C(=O)OC(C)(C)C)[CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CCOC(C)=O>CCOC(C)=O>[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][C@@H:12]([NH2:16])[CH2:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67128965HCID 67128965, compound

Product 1

HCID 28305814HCID 28305814, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl [(3R)-1-(3-phenylpropyl)-3-piperidinyl]carbamate (880 mg) in AcOEt (1.3 mL) was added 4N HCl—AcOEt (8.8 mL). The mixture was stirred at ambient temperature for 3 hours. The solvent was evaporated. Dichloromethane (10 ml) and saturated sodium bicarbonate (15 ml) was added. Aqueous layer was separated and extracted with dichloromethane. Combined organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo to give (3R)-1-(3-phenylpropyl)-3-piperidineamine (586 mg) as an yellow oil.

Workup

  1. customThe solvent was evaporated
  2. additionDichloromethane (10 ml) and saturated sodium bicarbonate (15 ml) was added
  3. customAqueous layer was separated
  4. extractionextracted with dichloromethane
  5. dry with materialCombined organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-ace0824d4d4949c594a9e76b00e8c51b
Source dataset
uspto-grants-2010_07
Patent number
US07750155B2

Reaction notes

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