Naphthalimide → HCID 131720205, compound

HRID 1379039

Reaction equation

HRID 1379039 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[CH:15]=[CH:16][CH:17]=[C:10]3[C:11]=2[C:6](=[CH:7][CH:8]=[CH:9]3)[C:5]1=[O:18].C1(=O)C2C3C(=CC=CC=3C(=[O:32])N1)C=CC=2.[F:34][C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[NH:40][CH:39]=[C:38]2[CH:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1.C(N1CCC(Cl)CC1)(OC(C)(C)C)=[O:51]>ClCCCl>[OH2:14].[OH2:32].[OH2:51].[OH2:14].[F:34][C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[NH:40][CH:39]=[C:38]2[CH:44]1[CH2:49][CH2:48][N:47]([CH2:2][CH2:3][N:4]2[C:13](=[O:14])[C:12]3[CH:15]=[CH:16][CH:17]=[C:10]4[C:11]=3[C:6](=[CH:7][CH:8]=[CH:9]4)[C:5]2=[O:18])[CH2:46][CH2:45]1

Participants

6

Reactant 4

HCID 66491NaphthalimideHCID 522559N-(2-Chloroethyl)-1,8-naphthalimide2×HCID 111386244-Chloro-piperidine-1-carboxylic acid tert-butyl esterHCID 117699295-fluoro-3-(piperidin-4-yl)-1H-indole

Product 1

HCID 131720205HCID 131720205, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1.2 g of 2-(2-chloroethyl)-2,3-dihydro-1H-benz[de]isoquinoline-1,3-dione ("A") [obtainable by reaction of 2,3-dihydro-1H-benz[de]isoquinoline-1,3-dione with 1,2-dichloroethane to give 2-(2-chloroethyl)-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 mixture is stirred at room temperature for 8 hours. Customary working up gives 2-[2-(4-(5-fluoro-3-indolyl)piperidino)ethyl]-2,3-dihydro-1H-benz[de]isoquinoline-1,3-dione, tetrahydrate, m.p. 235°.

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-0d896ffe3af942e9aaae1ec8e18598c8
Source dataset
uspto-grants-1997_09
Patent number
US05670511

Linked notes

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