Morpholine → [1-(2-Mercapto-3-morpholin-4-yl-propyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 1422788Notes

Reaction equation

HRID 1422788 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]([O:11][C:12](=[O:24])[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH:21]2[CH2:23][S:22]2)[CH2:16][CH2:15]1)([CH3:10])([CH3:9])[CH3:8]>C(O)C>[C:7]([O:11][C:12](=[O:24])[NH:13][CH:14]1[CH2:15][CH2:16][N:17]([CH2:20][CH:21]([SH:22])[CH2:23][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH2:18][CH2:19]1)([CH3:9])([CH3:8])[CH3:10]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86662008(1-Thiiranylmethyl-piperidin-4-yl)-carbamic acid tert-butyl ester

Product 1

HCID 86662007[1-(2-Mercapto-3-morpholin-4-yl-propyl)-piperidin-4-yl]-carbamic acid tert-butyl esterYield 134.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Morpholine (80 μL, 0.83 mmol, 1.5 eq) is added at room temperature to a stirred solution of (1-thiiranylmethyl-piperidin-4-yl)-carbamic acid tert-butyl ester (300 mg, 0.55 mmol, 1.0 eq) in ethanol (2 mL). The reaction mixture is irradiated under microwave conditions for 4 minutes at 140° C. and 80 W and then solvent is evaporated to afford [1-(2-mercapto-3-morpholin-4-yl-propyl)-piperidin-4-yl]-carbamic acid tert-butyl ester as an off-white semisolid (266 mg, 67% yield).

Workup

  1. customThe reaction mixture is irradiated under microwave conditions for 4 minutes at 140° C.
  2. custom80 W and then solvent is evaporated

Sources & evidence

ORD record
ord-86e8a4c02c894f03b89fbc93b0b671fc
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

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