Acetic Acid → tert-Butyl 4-(morpholin-4-yl)piperidine-1-carboxylate

HRID 1868114Notes

Reaction equation

HRID 1868114 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 14571198tert-Butyl 4-(morpholin-4-yl)piperidine-1-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (2.99 g, 15 mmole), morpholine (1.4 mL, 15.8 mmole), acetic acid (11.0 mL, 18 mmole) were dissolved in 30 mL dichloroethane and sodium triacetoxyborohydride (6.36 g, 30 mmole) was added and the reaction mixture was stirred at room temperature for 2 hours. The mixture was diluted with dichloromethane and then washed with 2N NaOH, water, and dried (MgSO4). Filtration and evaporation gave 3.84 g (95%) 4-morpholin-4-yl-piperidine-1-carboxylic acid tert-butyl ester as a colorless oil that solidified on standing.

Workup

  1. washwashed with 2N NaOH, water
  2. dry with materialdried (MgSO4)
  3. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-3ca8a6033f624d449703772494e2a62a
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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