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

HRID 2395130
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HRID 2395130 반응식
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
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21868444Ether tetrahydrofuran용매

실험 절차

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-methoxyethoxymethoxymethyl)-10-methylphenothiazine-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.

후처리

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

출처 및 근거

ORD 기록
ord-ee642b2ba141449e8d9f90afb11447da
출처 데이터셋
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05811389

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