Triethylamine → Benzyl 3-(3-hydroxypropyl)piperidine-1-carboxylate

HRID 2038168Notes

Reaction equation

HRID 2038168 reaction equation
[C:1]1([CH2:7][O:8][C:9]([O:11]N2C(=O)CCC2=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH:21]([CH2:25][CH2:26][CH2:27][OH:28])[CH2:20]1.C(N(CC)CC)C>ClCCl>[OH:28][CH2:27][CH2:26][CH2:25][CH:21]1[CH2:22][CH2:23][CH2:24][N:19]([C:9]([O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:11])[CH2:20]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 47124763-Piperidin-3-ylpropan-1-ol

Product 1

HCID 58306111Benzyl 3-(3-hydroxypropyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-({[(Phenylmethyl)oxy]carbonyl}oxy)-2,5-pyrrolidinedione (commercially available, for example, from Aldrich) (8.70 g, 34.9 mmol) was added portionwise to a stirred mixture of 3-(3-piperidinyl)-1-propanol (commercially available, for example, from Astatech) (5.02 g, 35 mmol) and triethylamine (5 mL, 3.63 g, 35.9 mmol) in dichloromethane (100 mL) at room temperature. The resultant mixture was allowed to stand at room temperature for 18 hours. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate (100 mL). The organic phase was dried (MgSO4), filtered and evaporated. The sample was purified by chromatography on silica (100 g cartridge loaded in dichloromethane) using a gradient of 0-100% ethyl acetate-cyclohexane over 40 minutes. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a colourless liquid (8.45 g).

Workup

  1. customat room temperature
  2. washThe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate (100 mL)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe sample was purified by chromatography on silica (100 g cartridge loaded in dichloromethane)
  7. customover 40 minutes
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-a92a9731b99c4d77a7492ff2aa5f6338
Source dataset
uspto-grants-2013_11
Patent number
US08575340B2

Reaction notes

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