Triethylamine → 4-(2,2-Dimethylcyclopropanecarbonylamino)-1-benzylpiperidine

HRID 1007118Notes

Reaction equation

HRID 1007118 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:22][C:23]1([CH3:29])[CH2:25][CH:24]1[C:26](Cl)=[O:27]>ClCCl>[CH3:22][C:23]1([CH3:29])[CH2:25][CH:24]1[C:26]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1)=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4158521-Benzyl-4-piperidylamineHCID 110079512,2-Dimethylcyclopropanecarbonyl chloride

Product 1

HCID 99219574-(2,2-Dimethylcyclopropanecarbonylamino)-1-benzylpiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-amino-1-benzylpiperidine (100 mg, 0.526 mmol) was dissolved into dichloromethane (10 ml) and then added with triethylamine (150 mg, 1.5 mmol) and 2,2-dimethylcyclopropanecarbonylchloride (159 mg, 1.2 mmol), which was further stirred at the room temperature for 14 hours. After the reaction was completed, the resultant was extracted with ethyl acetate and then washed, dried and concentrated according to the conventional manner and purified by using silica gel column chromatography (ethyl acetate, hexane), thus obtained a white crystal of 4-(2,2-dimethylcyclopropanecarbonylamino)-1-benzylpiperidine. The white crystal was dissolved into an ethanol (10 ml)-ethyl acetate (1 ml) mixed solvent, wherein 5% palladium carbon (150 mg) and formic acid (160 mg) were dissolved into the ethanol (10 ml) and applied thereto with dropping, which was stirred at the room temperature over night. After the palladium was filtered, the solvent was distilled out and aqueous solution of 2M sodium hydroxide was added therein to make pH>13, the solution was extracted with dichloromethane and further washed with a saturated saline solution, dried and vacuum concentrated, thus obtained 4-(2,2-dimethylcyclopropanecarbonylamino)piperidine (23:R =2,2-dimethylcyclopropane) (11.2 mg, 11%).

Workup

  1. extractionthe resultant was extracted with ethyl acetate
  2. washwashed
  3. customdried
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-d948480ff4594c0b80f68576a90ed092
Source dataset
uspto-grants-2004_09
Patent number
US06794378B2

Reaction notes

Loading…