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

HRID 2395130
ノート
印刷プレビュー

反応式

HRID 2395130 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21868444Ether tetrahydrofuran溶媒

実験手順

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.

後処理

  1. customThe crude 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-ee642b2ba141449e8d9f90afb11447da
出典データセット
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05811389

反応ノート

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