Chloroform → 3-Fluoro-10-[4-(3-hydroxypropyl)piperazino]-8-isopropyl-10,11-dihydrodibenzo (b,f) thiepin

HRID 1389277Notes

Reaction equation

HRID 1389277 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[C:9]3[CH:19]=[C:20]([CH:23]([CH3:25])[CH3:24])[CH:21]=[CH:22][C:8]=3[S:7][C:6]=2[CH:26]=1.[OH:27][CH2:28][CH2:29]CN1CCNCC1.C(Cl)(Cl)Cl>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH:10]([N:12]3[CH2:13][CH2:14][N:15]([CH2:18][CH2:29][CH2:28][OH:27])[CH2:16][CH2:17]3)[C:9]3[CH:19]=[C:20]([CH:23]([CH3:24])[CH3:25])[CH:21]=[CH:22][C:8]=3[S:7][C:6]=2[CH:26]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 79207Piperazin-1-ylpropanolHCID 30541663-Fluoro-8-isopropyl-10-(4-methylpiperazino)-10,11-dihydrodibenzo(b,f)thiepin

Product 1

HCID 130761743-Fluoro-10-[4-(3-hydroxypropyl)piperazino]-8-isopropyl-10,11-dihydrodibenzo (b,f) thiepin

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.0 g 10-chloro-3-fluoro-8-isopropyl-10,11-dihydrodibenzo (b,f) thiepin (Example 1), 4.0 g 1-(3-hydroxypropyl) piperazine (T. Zawisa et al., Acta Polon. Pharm. 22, 477, 1965) and 7 ml of chloroform was refluxed for 5 hours and then processed in the manner described in Example 2. 4.4 g (76%) of an oily base which was converted to a crystalline dimaleate, m.p. 106°-108° C. (ethanol) was obtained.

Workup

  1. temperaturewas refluxed for 5 hours

Sources & evidence

ORD record
ord-4918a5b5d2d146c69c34c3f844966515
Source dataset
uspto-grants-1981_01
Patent number
US04243805

Reaction notes

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