Triethylamine → HCID 22278907, compound

HRID 1865246Notes

Reaction equation

HRID 1865246 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C:9]1([CH3:22])[CH3:21].C(N(CC)CC)C>C(Cl)Cl>[CH2:14]([N:11]1[CH2:12][CH2:13][CH:8]([NH:7][C:2]([O:4][CH2:5][CH3:6])=[O:3])[C:9]([CH3:22])([CH3:21])[CH2:10]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 102361061-Benzyl-3,3-diMethyl-piperidin-4-aMine

Product 1

HCID 22278907HCID 22278907, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chloroformate (2 ml) was added to a stirred solution of 4-amino-1-benzyl-3,3-dimethylpiperidine (1.6 g, 7.33 mmol) and triethylamine (2 ml) in methylene chloride (25 ml) at ambient temperature, stirring was continued for 1 hr concentrated to dryness, triturated with water, extracted with ethyl acetate, dried (Na2SO4) and concentrated to give 1-benzyl-4-carbethoxyamino-3,3-dimethyl piperidine as oil. Yield 1.3 g (62%), C17H26N2O2, m/z 291 (M+1), PMR (CDCl3): 0.98 (s, 3H), 1.2 (t, 6H), 1.78 (m, 2H), 2.42 (m, 2H), 2.82 (m, 2H), 3.6 (d, 2H), 3.9 (m, 1H), 4.1 (q, 2H), 4.8 (bs, 1H), 7.54 (m, 5H).

Workup

  1. concentrationconcentrated to dryness
  2. customtriturated with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9ed69adce7e144eaa8d27ce5a4a8a516
Source dataset
uspto-grants-2009_12
Patent number
US07626032B2

Reaction notes

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