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

HRID 1982161노트

반응식

HRID 1982161 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-f499cc9cb1084c9d974773bb0917644d
출처 데이터셋
uspto-grants-1986_06
특허 번호
US04595689

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