Morpholine → HCID 68968810, compound

HRID 1726312Notes

Reaction equation

HRID 1726312 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:23]2[CH:28]=[CH:27][C:26](Br)=[CH:25][CH:24]=2)[CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:21]=2[CH3:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:21]=2[CH3:22])[C:23]2[CH:28]=[CH:27][C:26]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)=[CH:25][CH:24]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23665647Potassium tert-butoxideHCID 68972871HCID 68972871, compound

Product 1

HCID 68968810HCID 68968810, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

A solution of 4-[(4-bromo-phenyl)-(4-methyl-pyridin-3-ylmethyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (see EXAMPLE 352) (300 mg, 0.630 mmol), Pd(OAc)2 (7.10 mg, 0.0315 mmol), potassium tert-butoxide (106 mg, 0.945 mmol), morpholine (50.0 μL, 0.573 mmol) and tri(tert-butyl)phosphine (128 mg, 0.0315 mmol) in degassed toluene (2.2 mL) was stirred at 100° C. for 16 hours under nitrogen. Standard work-up and purification gave 4-[(4-methyl-pyridin-3-ylmethyl)-(4-morpholin-4-yl-phenyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester as a white solid (191 mg, 74%).

Workup

  1. customStandard work-up and purification

Sources & evidence

ORD record
ord-52f46f47235f49d0b25e112c647b593c
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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