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

HRID 2395182노트

반응식

HRID 2395182 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21868444Ether tetrahydrofuran용매

실험 절차

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.

후처리

  1. customThe 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-7359a4c3ede94ec3bed85935e45962d6
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05811548

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