4-Chloro-piperidine-1-carboxylic acid tert-butyl ester → HCID 131720206, compound

HRID 1379043Notes

Reaction equation

HRID 1379043 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][N:5]1[C:14](=[O:15])[C:13]2[CH:16]=[CH:17][CH:18]=[C:11]3[C:12]=2[C:7](=[CH:8][CH:9]=[CH:10]3)[C:6]1=[O:19].[F:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]2[CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(N1CCC(Cl)CC1)(OC(C)(C)C)=O>>[OH2:4].[ClH:1].[F:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]2[CH:30]1[CH2:35][CH2:34][N:33]([CH2:2][CH2:3][O:4][N:5]2[C:14](=[O:15])[C:13]3[CH:16]=[CH:17][CH:18]=[C:11]4[C:12]=3[C:7](=[CH:8][CH:9]=[CH:10]4)[C:6]2=[O:19])[CH2:32][CH2:31]1

Participants

4

Reactant 3

HCID 111386244-Chloro-piperidine-1-carboxylic acid tert-butyl esterHCID 117699295-fluoro-3-(piperidin-4-yl)-1H-indoleHCID 22909408HCID 22909408, compound

Product 1

HCID 131720206HCID 131720206, compound

Procedure

1.2 9 of 2-(2-chloroethoxy)-2,3-dihydro-1H-benz[de]isoquinoline-1,3-dione ("D") [obtainable by reaction of N-hydroxy-2,3-dihydro-1H-benz[de]isoquinoline-1,3-dione with 1,2-dichloroethane to give 2-(2-chloroethoxy)-2,3-dihydro-1H-benz[de]isoquinoline-1,3-dione] and 1.0 g of 4-(5-fluoroindol-3-yl)piperidine [obtainable by reaction of N-BOC-4-chloropiperidine with 5-fluoroindole and subsequent removal of the protective group] are dissolved in 200 ml of acetonitrile and the solution is stirred at room temperature for 8 hours. Customary working up gives 2-[2-(4-(5-fluoro-3-indolyl)piperidino)ethoxy]-2,3-dihydro-1H-benz[de]isoquinoline-1,3-dione, hydrochloride hydrate, m.p. 271°.

Workup

  1. customwith 5-fluoroindole and subsequent removal of the protective group]
  2. dissolutionare dissolved in 200 ml of acetonitrile

Sources & evidence

ORD record
ord-115245c8b72041f9819c46fdc252e1d2
Source dataset
uspto-grants-1997_09
Patent number
US05670511

Reaction notes

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