Hydrochloric Acid → Dihydrolenperone

HRID 866867Notes

Reaction equation

HRID 866867 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH:19]([CH:22]([OH:30])[C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[CH2:18][CH2:17]3)OCC[O:9]2)=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>C(Cl)(Cl)Cl>[F:29][C:26]1[CH:27]=[CH:28][C:23]([CH:22]([CH:19]2[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][CH2:13][C:8](=[O:9])[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:17][CH2:18]2)[OH:30])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20318877HCID 20318877, compound

Product 1

HCID 100146Dihydrolenperone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3.0 g. (0.0072 mole) of 2-(p-fluorophenyl)-2-{3-[4-(p-fluoro-α-hydroxybenzyl)piperidino]propyl}-1,3-dioxolane in 5 ml. of chloroform was stirred at room temperature with 25 ml. of 6N hydrochloric acid for 2 hr. The mixture was poured onto crushed ice and an excess of 50% sodium hydroxide solution was added. The free base of the ketone crystallized upon neutralization. The solid which was obtained was recrystallized from benzene-isooctane and gave 1 g. of white solid melting at 144°-146° C.

Workup

  1. additionThe mixture was poured
  2. customonto crushed ice
  3. customThe free base of the ketone crystallized upon neutralization
  4. customThe solid which was obtained
  5. customwas recrystallized from benzene-isooctane
  6. customgave 1 g

Sources & evidence

ORD record
ord-8965c153425241d581641e8978e3775b
Source dataset
uspto-grants-1978_07
Patent number
US04101662

Reaction notes

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