1-Piperidinecarboxaldehyde → 10-Hexyl-3,7-dimethoxy-phenothiazine-4-carbaldehyde

HRID 2395134Notes

Reaction equation

HRID 2395134 reaction equation
[CH2:1]([N:7]1[C:20]2[CH:19]=[CH:18][C:17]([O:21][CH3:22])=[CH:16][C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[C:11]([O:23][CH3:24])[CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C([Li])CCC.[CH:30](N1CCCCC1)=[O:31]>C(OCC)C.O1CCCC1>[CH2:1]([N:7]1[C:8]2[CH:9]=[CH:10][C:11]([O:23][CH3:24])=[C:12]([CH:30]=[O:31])[C:13]=2[S:14][C:15]2[C:20]1=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 174291-PiperidinecarboxaldehydeHCID 1897249610-Hexyl-3,7-dimethoxy-phenothiazineHCID 178418339Butyllithium

Product 1

HCID 1897260610-Hexyl-3,7-dimethoxy-phenothiazine-4-carbaldehydeYield 64.4%

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent

Procedure

A solution of 3.42 g (10.0 mmol) of 10-hexyl-3,7-dimethoxy-phenothiazine in 50 ml of diethyl ether/tetrahydrofuran (4:1) was reacted with 8.12 ml of n-butyllithium solution (1.6M in hexane) and 3.35 g (29.6 mmol) of N-formylpiperidine analogously to that described in Example 4.1.1.c. The product was chromatographed on silica gel with ethyl acetate/hexane (1:4), whereupon 2.39 g (64.4%) of 10-hexyl-3,7-dimethoxy-phenothiazine-4-carbaldehyde were obtained as a red oil.

Workup

  1. customThe product was chromatographed on silica gel with ethyl acetate/hexane (1:4)

Sources & evidence

ORD record
ord-b79ee955c69b4f9383b50c2ddf80b2a8
Source dataset
uspto-grants-1998_09
Patent number
US05811389

Reaction notes

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