Hydrochloric Acid → Ethyl 1-acetyl-5-(cyclohexylmethyl)piperidine-3-carboxylate

HRID 1696285Notes

Reaction equation

HRID 1696285 reaction equation
C(N(CC)CC)C.[CH:8]1([CH2:14][CH:15]2[CH2:20][NH:19][CH2:18][CH:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[C:26](Cl)(=[O:28])[CH3:27].Cl>C(Cl)Cl>[C:26]([N:19]1[CH2:20][CH:15]([CH2:14][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:16][CH:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18]1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66844627Ethyl 5-(cyclohexylmethyl)piperidine-3-carboxylate

Product 1

HCID 66844834Ethyl 1-acetyl-5-(cyclohexylmethyl)piperidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (410 μL, 2.9 mmol) was added to a solution of ethyl 5-(cyclohexylmethyl)piperidine-3-carboxylate (180 mg, 0.71 mmol) and acetyl chloride (120 mg, 1.4 mmol) in CH2Cl2 (10 mL). The reaction was maintained at room temperature for 30 min before being diluted with CH2Cl2 (20 mL) and poured into HCl (1 N, 20 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined organic layers were sequentially washed with H2O (10 mL) and brine before being dried over Na2SO4. Concentration under reduced pressure and purification by silica gel chromatography (hexane→80% EtOAc/hexane) provided the title compound as a yellow oil. MS m/z: 296.1 (M+1).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  3. washThe combined organic layers were sequentially washed with H2O (10 mL) and brine
  4. dry with materialbefore being dried over Na2SO4
  5. concentrationConcentration
  6. customunder reduced pressure and purification by silica gel chromatography (hexane→80% EtOAc/hexane)

Sources & evidence

ORD record
ord-ff1dad69d0334471b90cb9ecf74a01cf
Source dataset
uspto-grants-2012_04
Patent number
US08163766B2

Reaction notes

Loading…