Triethylamine → 1236302-37-6

HRID 2177475Notes

Reaction equation

HRID 2177475 reaction equation
[CH3:1][CH:2]1[CH:7]([OH:8])[CH2:6][CH2:5][CH2:4][NH:3]1.C(N(CC)CC)C.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>ClCCl>[CH2:20]([O:19][C:17]([N:3]1[CH2:4][CH2:5][CH2:6][CH:7]([OH:8])[CH:2]1[CH3:1])=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 20300431HCID 20300431, compound

Product 1

HCID 594384841236302-37-6Yield 34.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.4 g (9.232 mmol) 2-methyl-piperidin-3-ol (CAS: 4766-56-7) in 9.8 ml dichloromethane under argon at room temperature, was added 2.57 ml (18.46 mmol) triethylamine. The mixture was stirred for 15 minutes and then cooled to 0° C. 1.37 ml (9.232 mmol) benzyl chloroformate was added dropwise. The reaction mixture was allowed to come to room temperature and the stirring was continued overnight. The mixture was extracted three times with water and the combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified with flash column chromatography on silica gel (Eluent: Heptane/ethyl acetate 0 to 30) to provide 800 mg (34.8%) of the title compound as a colorless oil. MS (m/e): 272.4 (M+Na+)

Workup

  1. customto come to room temperature
  2. waitthe stirring was continued overnight
  3. extractionThe mixture was extracted three times with water
  4. dry with materialthe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified with flash column chromatography on silica gel (Eluent: Heptane/ethyl acetate 0 to 30)

Sources & evidence

ORD record
ord-f4de2e9d851542c19f1fa10a820cc205
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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