Sodium Carbonate → [1-(2-Hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 2267678Notes

Reaction equation

HRID 2267678 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:22][CH2:23][OH:24]>CO>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:22][CH2:23][OH:24])[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 108982-BromoethanolHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 45076484[1-(2-Hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of piperidin-4-yl-carbamic acid tert-butyl ester 3 (10 g, 50 mmol) in 100 ml of methanol are added sodium carbonate (21.2 g, 200 mmol) and 2-bromoethanol (7.1 ml, 100 mmol). The mixture is stirred over night. The solvents are then evaporated and the residue is triturated with DCM, filtered and evaporated again. The crude product is purified by chromatography using EtOAc/MeOH (saturated with ammonia): 9/1.

Workup

  1. customThe solvents are then evaporated
  2. customthe residue is triturated with DCM
  3. filtrationfiltered
  4. customevaporated again
  5. customThe crude product is purified by chromatography

Sources & evidence

ORD record
ord-b89318ca49ba446da2dcaf780f85275c
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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