1-(2-Hydroxyethyl)piperazine → HCID 12271968, compound

HRID 1732761Notes

Reaction equation

HRID 1732761 reaction equation
[F:1][C:2]1[C:23]([F:24])=[CH:22][C:5]2[CH:6]([N:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[S:10][C:4]=2[CH:3]=1.[OH:25][CH2:26]CN1CCNCC1>C(Cl)(Cl)Cl>[F:1][C:2]1[C:23]([F:24])=[CH:22][C:5]2[CH:6]([N:15]3[CH2:16][CH2:17][N:18]([CH2:21][CH2:26][OH:25])[CH2:19][CH2:20]3)[CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[S:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 12271965HCID 12271965, compound

Product 1

HCID 12271968HCID 12271968, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 7,8-difluoro-10-chloro-10,11-dihydrodibenzo(b,f)thiepine (see Example 15) (6.35 g), 1-(2-hydroxyethyl)-piperazine (6.1 g) and chloroform (10 ml) was refluxed for 7.5 hours under stirring. The chloroform was evaporated under diminished pressure, the residue dissolved in benzene (200 ml) and the solution thoroughly washed with water and shaken with 3 N-HCl (150 ml). The precipitated hydrochloride was filtered, added to the aqueous layer of the filtrate and the resultant suspension made alkaline by addition of ammonium hydroxide. The liberated base was taken up in benzene and the extract yielded 7.1 g (84%) of the desired oily base. This was crystallized from aqueous acetone in the form of the hemihydrate, which in the pure state melts at 101°-102° C.

Workup

  1. temperaturewas refluxed for 7.5 hours
  2. customThe chloroform was evaporated under diminished pressure
  3. dissolutionthe residue dissolved in benzene (200 ml)
  4. washthe solution thoroughly washed with water
  5. stirringshaken with 3 N-HCl (150 ml)
  6. filtrationThe precipitated hydrochloride was filtered
  7. additionadded to the aqueous layer of the filtrate
  8. additionby addition of ammonium hydroxide
  9. customthe extract yielded 7.1 g (84%) of the desired oily base
  10. customThis was crystallized from aqueous acetone in the form of the hemihydrate, which in the pure state melts at 101°-102° C.

Sources & evidence

ORD record
ord-27031988c91e4979b912b5237d5006a7
Source dataset
uspto-grants-1980_12
Patent number
US04238611

Reaction notes

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