Triethylamine → Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 220829Notes

Reaction equation

HRID 220829 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:16]([O:23][C:24](Cl)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[CH2:16]([O:23][C:24]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 4207714-Piperidinemethanol

Product 1

HCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylateYield 77.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Piperidinemethanol (5.0 g, 43 mmol) was dissolved in dichloromethane (100 ml) and triethylamine (12 ml, 86 mmol) at 0° C. Benzylchloroformate (6.8 ml, 47.3 mmol) was added and the mixture was stirred for 20 h at room temperature then solvents were removed in vacuo. The residue was redissolved in EtOAc, washed with 1M KHSO4, water then brine, dried and concentrated in vacuo to yield the title compound (8.33 g, 77%).

Workup

  1. customat 0° C
  2. customsolvents were removed in vacuo
  3. dissolutionThe residue was redissolved in EtOAc
  4. washwashed with 1M KHSO4, water
  5. dry with materialbrine, dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-35cccfc29ede41b78bef529063086ea2
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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