Sodium Hydroxide → HCID 20232494, compound

HRID 2290474Notes

Reaction equation

HRID 2290474 reaction equation
[CH2:1]([N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33]CCCC)=[O:32])=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH-].[Na+]>CO>[CH2:1]([N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20232681HCID 20232681, compound

Product 1

HCID 20232494HCID 20232494, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 16.0 g. (30 mmole) n-butyl 3-[4-(1-n-hexadecylpiperazin-4-yl)-phenyl]-propionate, 125 ml. 1N aqueous sodium hydroxide solution and 125 ml. methanol is stirred for 6 hours at 60° C. and the methanol subsequently distilled off. Crystals precipitate out from the cold aqueous phase, which are filtered off with suction and washed with water. They are dissolved in hot water and the hydrochloride is precipitated with 2N hydrochloric acid. After suction filtration, washing with water and drying, the yield is 13.0 g. (85% of theory); m.p. 218°-220° C. When recrystallised from methanol, with the addition of a little water, the hydrochloride melts at 219°-221° C.

Workup

  1. additionA mixture of 16.0 g
  2. distillationthe methanol subsequently distilled off
  3. customCrystals precipitate out from the cold aqueous phase, which
  4. filtrationare filtered off with suction
  5. washwashed with water
  6. dissolutionThey are dissolved in hot water
  7. customthe hydrochloride is precipitated with 2N hydrochloric acid
  8. filtrationAfter suction filtration
  9. washwashing with water
  10. customdrying
  11. customWhen recrystallised from methanol, with the addition of a little water

Sources & evidence

ORD record
ord-accd881296fe48048718ed3f1cbc3702
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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