1-Piperidinecarboxaldehyde → [10-Hexyl-3,7-dimethoxy-6-(2-methoxyethoxymethoxymethyl)-phenothiazin-4-yl]-methanol

HRID 2395182Notes

Reaction equation

HRID 2395182 reaction equation
C(N1C2C=CC(OC)=C(COCOCCOC)C=2SC2C1=CC=C(OC)C=2)CCCCC.C([Li])CCC.C(N1CCCCC1)=O.[CH3:46][O:47][C:48]1[CH:49]=[CH:50][C:51]2[N:52]([CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH3:79])[C:53]3[C:58]([S:59][C:60]=2[C:61]=1[CH:62]=[O:63])=[C:57]([CH2:64][O:65][CH2:66][O:67][CH2:68][CH2:69][O:70][CH3:71])[C:56]([O:72][CH3:73])=[CH:55][CH:54]=3.[BH4-].[Li+]>C(OCC)C.O1CCCC1.O1CCCC1>[CH2:74]([N:52]1[C:51]2[CH:50]=[CH:49][C:48]([O:47][CH3:46])=[C:61]([CH2:62][OH:63])[C:60]=2[S:59][C:58]2[C:53]1=[CH:54][CH:55]=[C:56]([O:72][CH3:73])[C:57]=2[CH2:64][O:65][CH2:66][O:67][CH2:68][CH2:69][O:70][CH3:71])[CH2:75][CH2:76][CH2:77][CH2:78][CH3:79]

Participants

8

Reactant 5

HCID 174291-PiperidinecarboxaldehydeHCID 4148881Lithium borohydrideHCID 1897254710-Hexyl-3,7-dimethoxy-4-(2-methoxyethoxymethoxymethyl)-phenothiazineHCID 189725573,7-Dimethoxy-10-hexyl-6-(2-methoxyethoxymethoxymethyl)phenothiazine-4-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 18972580[10-Hexyl-3,7-dimethoxy-6-(2-methoxyethoxymethoxymethyl)-phenothiazin-4-yl]-methanolYield 51.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21868444Ether tetrahydrofuranSolvent

Procedure

A solution of 8.0 g (17.33 mmol) of 10-hexyl-3,7-dimethoxy-4-(2-methoxy-ethoxymethoxymethyl)-phenothiazine in 100 ml of diethyl ether/tetrahydrofuran (4:1) was reacted with 12.0 ml of n-butyllithium solution (1.6M in hexane) and 2.94 g (26.0 mmol) of N-formylpiperidine analogously to that described in Example 4.1.1.c. The resulting 3,7-dimethoxy-10-hexyl-6-(2-methoxyethoxymethoxymethyl)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 product was chromatographed on silica gel with ethyl acetate/hexane (1:1), whereupon, after drying in a high vacuum, 4.41 g (51.7%) of [10-hexyl-3,7-dimethoxy-6-(2-methoxyethoxymethoxymethyl)-phenothiazin-4-yl]-methanol were obtained as a light yellowish oil.

Workup

  1. customThe 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-7359a4c3ede94ec3bed85935e45962d6
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

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