Acetyl chloride → Racemic (2'S,3S,4'R)-4'-[2-(1-acetyl-4-piperidinyloxy)-5-bromo-phenyl]-6-chloro-2'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 504510Notes

Reaction equation

HRID 504510 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[C:6]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)[C:9]32[C:29]2[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=2)[NH:23][C:22]3=[O:31])[CH:7]=1.[C:39](Cl)(=[O:41])[CH3:40].C(N(CC)CC)C>O1CCCC1>[C:39]([N:36]1[CH2:37][CH2:38][CH:33]([O:32][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][C:6]=2[CH:8]2[CH2:13][C:12](=[O:14])[NH:11][CH:10]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)[C:9]32[C:29]2[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=2)[NH:23][C:22]3=[O:31])[CH2:34][CH2:35]1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 74928458Racemic (2'S,3S,4'R)-4'-[5-bromo-2-(4-piperidinyloxy)-phenyl]-6-chloro-2'-(5-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Product 1

HCID 77285149Racemic (2'S,3S,4'R)-4'-[2-(1-acetyl-4-piperidinyloxy)-5-bromo-phenyl]-6-chloro-2'-(3-chlorophenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneYield 46.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to the method described in Example 38b, racemic (2′S,3S,4′R)-4′-[5-bromo-2-(4-piperidinyloxy)-phenyl]-6-chloro-2′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (85 mg, 0.14 mmol) was reacted with acetyl chloride (13 mg, 0.17 mmol), triethylamine in tetrahydrofuran to give the title compound as a white solid (Yield: 43 mg).

Sources & evidence

ORD record
ord-52e7894c1307492b8d95153fbe8c062a
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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