Hydrogen Bromide → HCID 20353218, compound

HRID 372103Notes

Reaction equation

HRID 372103 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]2[CH:20]3[CH2:21][C:7]4([CH2:11][N:10]([CH2:12][CH:13]5[CH2:17][CH2:16][CH2:15][CH2:14]5)[CH2:9][CH:8]4[C:18]4[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=43)[C:6]=2[CH:26]=1.N([O-])=O.[Na+].[BrH:31]>O>[Br:31][C:2]1[CH:3]=[CH:4][C:5]2[CH:20]3[CH2:21][C:7]4([CH2:11][N:10]([CH2:12][CH:13]5[CH2:17][CH2:16][CH2:15][CH2:14]5)[CH2:9][CH:8]4[C:18]4[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=43)[C:6]=2[CH:26]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 20353202HCID 20353202, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20353218HCID 20353218, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 5.0 g (14.55 mmoles) of 5-amino-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole, (Example 64), in 25 ml of 40% hydrobromic acid, cooled at 5°, was diazotized with a solution of 1.1 g (16 mmoles) of sodium nitrite in 5 ml of water. The reaction mixture was allowed to warm to room temperature, filtered, and then added dropwise to a solution of 4.0 g (27.7 mmoles) of cuprous bromide in 25 ml of 48% hydrobromic acid. After standing overnight, dilution with water gave a precipitate which was collected by filtration. The solids were extracted with methylene chloride, and the organic layer washed with 1N aqueous sodium hydroxide solution was then with water. The extract was dried over potassium carbonate and evaporated to give 1.2 g of 5-bromo-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]-cyclohepta[1,2-c]pyrrole as an oil; nmr spectrum δ 1.0-4.0 (m, 19); 6.8-7.5 (m, 7).

Workup

  1. filtrationfiltered
  2. filtrationwas collected by filtration
  3. extractionThe solids were extracted with methylene chloride
  4. washthe organic layer washed with 1N aqueous sodium hydroxide solution
  5. dry with materialThe extract was dried over potassium carbonate
  6. customevaporated

Sources & evidence

ORD record
ord-02eeba216bf940f0bc8b98cedda50625
Source dataset
uspto-grants-1978_05
Patent number
US04088772

Reaction notes

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