Hydrochloric Acid → HCID 13450868, compound

HRID 1155098Notes

Reaction equation

HRID 1155098 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]2[CH2:8][CH:9]3[CH2:14][N:13]([C:6]=2[CH:5]=1)[CH2:12][CH2:11][NH:10]3)([O-:3])=[O:2].[CH2:17](Br)[CH:18]=[CH2:19].C(=O)(O)[O-].[Na+].Cl>C(OCC)(=O)C.CN(C)C=O>[CH2:19]([N:10]1[CH:9]2[CH2:14][N:13]([C:6]3[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:16]=[CH:15][C:7]=3[CH2:8]2)[CH2:12][CH2:11]1)[CH:18]=[CH2:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 12764430HCID 12764430, compound

Product 1

HCID 13450868HCID 13450868, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9-nitro-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (17.5 g.), allyl bromide (7.6 ml.), sodium bicarbonate (1 teaspoon) and N,N-dimethylformamide (200 ml.) was stirred overnight at room temperature, then concentrated to dryness. The residue was partitioned between dilute aqueous sodium hydroxide and isopropyl acetate. The isopropyl acetate layer was washed with dilute aqueous sodium hydroxide and brine, filtered and concentrated to dryness. The residue was recrystallized from isopropyl alcohol, and the product was combined with corresponding product (2.3 g.) from a previous a preparation. Ethereal hydrogen chloride was added to a solution of the combined products in ethyl acetate affording 4-allyl-9-nitro-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (10 g.), the compound of Formula IV wherein Q is allyl.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was partitioned between dilute aqueous sodium hydroxide and isopropyl acetate
  3. washThe isopropyl acetate layer was washed with dilute aqueous sodium hydroxide and brine
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was recrystallized from isopropyl alcohol
  7. customa preparation

Sources & evidence

ORD record
ord-5b0a9f894e0046a8adef1bd25a8fd434
Source dataset
uspto-grants-1981_11
Patent number
US04299830

Reaction notes

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