Sodium borohydride → 4-(8-Bromodibenz[b,f]oxepin-10-yl)-1,2,3,6-tetrahydro-1-methylpyridine

HRID 1982161ノート

反応式

HRID 1982161 の反応式
[I-].[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[O:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[CH:9]=[C:8]([C:17]3[CH:22]=[CH:21][N+:20]([CH3:23])=[CH:19][CH:18]=3)[C:7]=2[CH:24]=1.[BH4-].[Na+]>CO.O>[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[O:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[CH:9]=[C:8]([C:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH:18]=3)[C:7]=2[CH:24]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 233174974-(8-Bromodibenz[b,f]oxepin-10-yl)-1-methylpyridinium iodide

生成物 1

HCID 136086144-(8-Bromodibenz[b,f]oxepin-10-yl)-1,2,3,6-tetrahydro-1-methylpyridine収率 99%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒2 回

実験手順

A stirred suspension of 4-(8-bromodibenz[b,f]oxepin-10-yl)-1-methylpyridinium iodide (2.7 g) in methanol (50 ml) was treated with sodium borohydride (1.04 g) and 15 ml of water. The mixture was stirred at ambient temperature for thirty minutes and then was diluted with 175 ml of water. The resulting solid was filtered off, washed with water and then was dissolved in dichloromethane (100 ml). The organic solution was washed with water, then was dried (potassium carbonate) and evaporated in vacuo. A solution of the residual solid in ethyl acetate (75 ml) was treated with a solution of maleic acid (0.64 g) in ethanol (5 ml). The crystalline product was recovered in two crops to give a total yield of 2.0 g of 4-(8-bromodibenz[b,f]oxepin-10-yl)-1,2,3,6-tetrahydro-1-methylpyridine, (Z)-2-butenedioate (1:1) salt, mp 186°-188°.

後処理

  1. filtrationThe resulting solid was filtered off
  2. washwashed with water
  3. dissolutionwas dissolved in dichloromethane (100 ml)
  4. washThe organic solution was washed with water
  5. dry with materialwas dried (potassium carbonate)
  6. customevaporated in vacuo
  7. additionA solution of the residual solid in ethyl acetate (75 ml) was treated with a solution of maleic acid (0.64 g) in ethanol (5 ml)
  8. customThe crystalline product was recovered in two crops

出典と根拠

ORDレコード
ord-f499cc9cb1084c9d974773bb0917644d
出典データセット
uspto-grants-1986_06
特許番号
US04595689

反応ノート

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