Acetic Acid → HCID 15662541, compound

HRID 2303932Notes

Reaction equation

HRID 2303932 reaction equation
N12CCC(CC1)/C(=[CH:9]\[N:10]1[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[S:17][C:16]3[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=3)/C2.[C:24](O)(=O)[CH3:25].[H][H]>[C].[Pd].CO>[CH:13]1[CH:14]=[CH:15][C:16]2[S:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[N:10]([CH2:9][C:24]34[CH2:25][CH2:9][N:10]([CH2:23][CH2:18]3)[CH2:11][CH2:12]4)[C:11]=2[CH:12]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9905165HCID 9905165, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15662541HCID 15662541, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

(E)-10-(1-Azabicyclo[2.2.2]oct-3-ylidenemethyl)phenothiazine (10.00 g, 0.0312 mol), acetic acid (2.25 g, 0.0374 mol) and 10% palladium carbon (2.00 g, water content 50%) were added to methanol (158 g) and the mixture was stirred under pressurization with hydrogen (3-5 kg/cm2, hydrogen gas amount:equimolar amount relative to starting material) at 45-50° C. for 8 hr. The obtained reaction mixture was subjected to HPLC. As a result, the starting material was not detected but highly pure mequitazine was quantitatively obtained.

Workup

  1. customThe obtained reaction mixture

Sources & evidence

ORD record
ord-a78f7c4e26ab45fcb6a8af82ac4f1891
Source dataset
uspto-grants-2002_08
Patent number
US06433168B1

Reaction notes

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