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

HRID 2395136ノート

反応式

HRID 2395136 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21868444Ether tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-74e73ea9d2a5493e8d92ede80153dd13
出典データセット
uspto-grants-1998_09
特許番号
US05811389

反応ノート

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