4-Methylmorpholine → Spiro[3h-indole-3,3'-piperidine]-2,6'(1h)-dione

HRID 1728012Notes

Reaction equation

HRID 1728012 reaction equation
Cl[C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:36])[C:10]3([CH:15](C4C=CC=C(Cl)C=4)[CH2:14][C:13](=[O:23])[N:12](CC(F)=O)[CH:11]3C3C=C(F)C=CC=3C)[C:5]2=[CH:4][CH:3]=1.CN1CCC(N)CC1.CN1CCOCC1>CN(C)C1C=CN=CC=1.O1CCCC1>[NH:12]1[C:13](=[O:23])[CH2:14][CH2:15][C:10]2([C:5]3[C:6](=[CH:7][CH:2]=[CH:3][CH:4]=3)[NH:8][C:9]2=[O:36])[CH2:11]1

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 27375314-Amino-1-methylpiperidineHCID 1317273276-chloro-4'-(3-chlorophenyl)-1'-[(fluorocarbonyl)-methyl]-2'-(5-fluoro-2-methylphenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Product 1

HCID 68614016Spiro[3h-indole-3,3'-piperidine]-2,6'(1h)-dioneYield 105.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in example 34b, racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-1′-[(fluorocarbonyl)-methyl]-2′-(5-fluoro-2-methylphenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (0.1 g, 0.18 mmol) prepared in example 57a was reacted with 1-methyl-piperidin-4-ylamine (0.1 g, 0.88 mmol), N-methylmorpholine (0.1 g, 0.99 mmol) and 4-dimethylaminopyridine (1 mg, 0.008 mmol) in tetrahydrofuran to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(5-fluoro-2-methylphenyl)-1′-[(1-methyl-piperidin-4-yl)aminocarbonyl)-methyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as an off-white solid (Yield 0.041 g, 36.7%).

Sources & evidence

ORD record
ord-8c294abae3cc4f5c96c2219bb49cf599
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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