4-Nitrophenethyl bromide → HCID 86745184, compound

HRID 346057Notes

Reaction equation

HRID 346057 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 86745184HCID 86745184, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-ba4990f2c03740a180e9f2573299be7d
Source dataset
uspto-grants-1991_10
Patent number
US05059688

Reaction notes

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