4-Morpholinecarbonyl chloride → Methyl [5-(4-ethylphenyl)-1-(morpholin-4-ylcarbonyl)piperidin-3-yl]carbamate

HRID 876307Notes

Reaction equation

HRID 876307 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH:11]([NH:15][C:16](=[O:19])[O:17][CH3:18])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2].[N:20]1([C:26](Cl)=[O:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:26]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:27])[CH2:12][CH:11]([NH:15][C:16](=[O:19])[O:17][CH3:18])[CH2:10]2)=[CH:5][CH:4]=1)[CH3:2]

Participants

3

Reactant 2

HCID 848104-Morpholinecarbonyl chlorideHCID 68074779Methyl [5-(4-ethylphenyl)piperidin-3-yl]carbamate

Product 1

HCID 68075447Methyl [5-(4-ethylphenyl)-1-(morpholin-4-ylcarbonyl)piperidin-3-yl]carbamateYield 32.1%

Procedure

170 mg (0.58 mmol) of methyl [5-(4-ethylphenyl)piperidin-3-yl]carbamate (Example 21A) and 113 mg (0.76 mmol, 1.3 eq.) of morpholine-4-carbonyl chloride were reacted according to General Method 3. Diastereomer separation of the cis/trans isomer mixture according to Method 7C gave 70 mg of the compound from Example 102.

Workup

  1. customDiastereomer separation of the cis/trans isomer mixture

Sources & evidence

ORD record
ord-8773ac48f44f4e5d880e8e2f45a7dd83
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

Loading…