Morpholine → HCID 67341747, compound

HRID 1670765Notes

Reaction equation

HRID 1670765 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:14](O)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.[OH-].[Na+]>CN(C)C=O.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:14]([N:44]2[CH2:49][CH2:48][O:47][CH2:46][CH2:45]2)=[O:15])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 8083MorpholineHCID 14798Sodium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7369171-((Tert-butoxy)carbonyl)-4-phenylpiperidine-4-carboxylic acid

Product 1

HCID 67341747HCID 67341747, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

1-(tert-Butoxycarbonyl)-4-phenylpiperidine-4-carboxylic acid (Bionet Co., 1.0 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (733 mg), 1-hydroxybenzotriazole (370 mg), morpholine (1 g) and triethylamine (0.76 ml) were dissolved in dimethylformamide (6 ml), and the mixture was stirred at room temperature for 10 hr. After completion of the reaction, 1N sodium hydroxide was added thereto. The precipitated solid was collected by filtration to give 4-(morpholin-4-ylcarbonyl)-4-phenyl-1-piperidinecarboxylic acid tert-butyl ester (907 mg, yield ds89%).

Workup

  1. additionwas added
  2. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-b54e9acfb95c422dbcf7dc6c6115afec
Source dataset
uspto-grants-2011_08
Patent number
US07994196B2

Reaction notes

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