Dichloromethane → Dimethyl 2-(cyclohexylmethyl)piperidine-1,4-dicarboxylate

HRID 1963127Notes

Reaction equation

HRID 1963127 reaction equation
[CH:1]1([CH2:7][CH:8]2[CH2:13][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11][CH2:10][NH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18](Cl)(=[O:21])[O:19][CH3:20].CCN(C(C)C)C(C)C.ClCCl>C(OCC)C>[CH:1]1([CH2:7][CH:8]2[CH2:13][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11][CH2:10][N:9]2[C:18]([O:19][CH3:20])=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66732253Methyl 2-(cyclohexylmethyl)piperidine-4-carboxylate

Product 1

HCID 86646598Dimethyl 2-(cyclohexylmethyl)piperidine-1,4-dicarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl 2-(cyclohexylmethyl)piperidine-4-carboxylate (1.79 g, 7.48 mmol), methyl carbonochloridate (1.06 g, 11.2 mmol) and DIPEA (1.93 g, 15.0 mmol) were added to dichloromethane (60 mL) at room temperature and stirred for 2 h. The reaction mixture was diluted with diethylether and washed with water. The organic phase was dried over MgSO4, filtered through Celite® and the solvent was evaporated. Crude product 2.2 g. 1H NMR (400 MHz, cdcl3) δ 0.71-0.97 (m, 2H), 1.02-1.28 (m, 5H), 1.38 (dt, 1H), 1.69 (ddd, 6H), 1.98 (ddd, 3H), 2.52-2.61 (m, 1H), 3.01-3.16 (m, 1H), 3.67 (s, 3H), 3.69 (s, 3H), 3.81-3.94 (m, 1H), 4.13-4.31 (m, 1H).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered through Celite®
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0e11839c06bb4b51afb492d879623649
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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