4-Nitrophenethyl bromide → HCID 86745184, 화합물

HRID 346057노트

반응식

HRID 346057 반응식
C(O)(=O)C(O)=O.[F:7][C:8]([F:28])([F:27])[C:9]1[CH:26]=[CH:25][C:12]([O:13][CH:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17][NH:16][CH2:15]2)=[CH:11][CH:10]=1.[N+](C1C=CC(CC[Br:38])=CC=1)([O-])=O.C(=O)(O)[O-].[Na+]>CN(C=O)C>[BrH:38].[F:28][C:8]([F:7])([F:27])[C:9]1[CH:26]=[CH:25][C:12]([O:13][CH:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17][NH:16][CH2:15]2)=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 792664-Nitrophenethyl bromideHCID 516892Sodium BicarbonateHCID 14348987HCID 14348987, 화합물

생성물 1

HCID 86745184HCID 86745184, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A mixture of 2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine of Example 1 (13.0 g, 0.042 mole), p-nitrophenethyl bromide (11.7 g, 0.05] mole), sodium bicarbonate (18 g, 0.21 mole) and 0.01 g of KI in DMF (100 ml) was warmed at 90° C. for six hours. The reaction mixture was cooled, filtered and concentrated to an oil which was stirred with water then extracted with ether. The ether extracts were washed with water and dried (saturated MgSO4). The solution was filtered then concentrated to an oil (20 g). The oil was passed through a silica gel dry column using ethyl acetate as the eluent. The desired produce was extracted with ethyl acetate, filtered and concentrated to an oil (16 g) which was dissolved in ether, then converted to the hydrobromide salt (8 g, 35%, m.p. 98°-108°) by the addition of ethereal HBr. A 3.0 g. sample was recrystallized from a 20:1 solution of ethyl acetate/methanol to yield 3-[2-p-nitrophenylethyl)]-2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)- 3-benzazepine hydrobromide (2.4 g, d 216°-217° C.).

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated to an oil which
  4. extractionthen extracted with ether
  5. washThe ether extracts were washed with water
  6. dry with materialdried (saturated MgSO4)
  7. filtrationThe solution was filtered
  8. concentrationthen concentrated to an oil (20 g)
  9. customdry column
  10. customThe desired produce
  11. extractionwas extracted with ethyl acetate
  12. filtrationfiltered
  13. concentrationconcentrated to an oil (16 g) which
  14. dissolutionwas dissolved in ether
  15. additionconverted to the hydrobromide salt (8 g, 35%, m.p. 98°-108°) by the addition of ethereal HBr
  16. customsample was recrystallized from a 20:1 solution of ethyl acetate/methanol

출처 및 근거

ORD 기록
ord-ba4990f2c03740a180e9f2573299be7d
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05059688

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