1-Piperidinecarboxaldehyde → [3,7-Dimethoxy-6-(2-methoxy-ethoxymethoxymethyl)-10-methyl-phenothiazin-4-yl]-methanol

HRID 2395177Notes

Reaction equation

HRID 2395177 reaction equation
COC1C=CC2N(C)C3C(SC=2C=1COCOCCOC)=CC(OC)=CC=3.C([Li])CCC.C(N1CCCCC1)=O.[CH3:41][O:42][C:43]1[CH:44]=[CH:45][C:46]2[N:47]([CH3:69])[C:48]3[C:53]([S:54][C:55]=2[C:56]=1[CH:57]=[O:58])=[C:52]([CH2:59][O:60][CH2:61][O:62][CH2:63][CH2:64][O:65][CH3:66])[C:51]([O:67][CH3:68])=[CH:50][CH:49]=3.[BH4-].[Li+]>C(OCC)C.O1CCCC1.O1CCCC1>[CH3:41][O:42][C:43]1[CH:44]=[CH:45][C:46]2[N:47]([CH3:69])[C:48]3[C:53]([S:54][C:55]=2[C:56]=1[CH2:57][OH:58])=[C:52]([CH2:59][O:60][CH2:61][O:62][CH2:63][CH2:64][O:65][CH3:66])[C:51]([O:67][CH3:68])=[CH:50][CH:49]=3

Participants

8

Reactant 5

HCID 174291-PiperidinecarboxaldehydeHCID 4148881Lithium borohydrideHCID 189724993,7-Dimethoxy-6-(2-methoxyethoxymethoxymethyl)-10-methylphenothiazine-4-carbaldehydeHCID 189725283,7-Dimethoxy-4-(2-methoxy-ethoxymethoxymethyl)-10-methyl-phenothiazineHCID 178418339Butyllithium

Product 1

HCID 18972627[3,7-Dimethoxy-6-(2-methoxy-ethoxymethoxymethyl)-10-methyl-phenothiazin-4-yl]-methanolYield 70.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21868444Ether tetrahydrofuranSolvent

Procedure

A solution of 8.31 g (21.73 mmol) of 3,7-dimethoxy-4-(2-methoxy-ethoxymethoxymethyl)-10-methyl-phenothiazine in 100 ml of diethyl ether/tetrahydrofuran (4:1) was reacted with 17.6 ml of n-butyllithium solution (1.6M in hexane) and 3.68 g (32.6 mmol) of N-formylpiperidine analogously to that described in Example 4.1.1.c. The resulting 3,7-dimethoxy-6-(2-methoxy-ethoxymethoxymethyl)-10-methyl-phenothiazine-4-carbaldehyde was dissolved in 100 ml of tetrahydrofuran and reduced with 22 ml of lithium borohydride solution (1M in tetrahydrofuran) analogously to that described in Example 4.1.8.b. The crude product was chromatographed on silica gel with ethyl acetate/hexane (1:1), whereupon, after drying in a high vacuum, 6.44 g (70.3%) of [3,7-dimethoxy-6-(2-methoxy-ethoxymethoxymethyl)-10-methyl-phenothiazin-4-yl]-methanol were obtained as light yellowish oil.

Workup

  1. customThe crude product was chromatographed on silica gel with ethyl acetate/hexane (1:1), whereupon
  2. customafter drying in a high vacuum

Sources & evidence

ORD record
ord-5e7d6312cafd4fcdadbd6bfcc47dfd1c
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

Loading…