Butyl bromide → HCID 19873454, compound

HRID 466375Notes

Reaction equation

HRID 466375 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][N:15]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[CH2:22]([Br:26])[CH2:23][CH2:24][CH3:25]>C(#N)C>[Br-:26].[CH2:22]([N+:15]1([CH2:14][CH2:13][CH2:12][C:9]2[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:11][CH:10]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 8002Butyl bromideHCID 19873372HCID 19873372, compound

Product 1

HCID 19873454HCID 19873454, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.35 g (4.35 mmol) of hexahydro-1-[3-[4-(methylsulfonylamino)phenyl]propyl]-1H-azepine, (Table 5, Entry 7) and 4.7 ml of n-butyl bromide in 10 ml of acetonitrile is heated at 80°-90° C. (oil bath temperature) for 20 hrs. The reaction is concentrated and the residue is partitioned between water and methylene chloride. The aqueous layer (50 ml) is extracted with methylene chloride and then basified with sodium hydroxide to at least pH 12. The solution is saturated with potassium bromide and then reextracted with methylene chloride. The aqueous layer is acidified with hydrobromic acid and lyophilized. Solids are extracted with 5% methanol-methylene chloride, concentrated, and the residue extracted into methylene chloride (filtered through cotton) and concentrated to yield the title compound.

Workup

  1. temperatureis heated at 80°-90° C. (oil bath temperature) for 20 hrs
  2. concentrationThe reaction is concentrated
  3. customthe residue is partitioned between water and methylene chloride
  4. extractionThe aqueous layer (50 ml) is extracted with methylene chloride
  5. extractionSolids are extracted with 5% methanol-methylene chloride
  6. concentrationconcentrated
  7. extractionthe residue extracted into methylene chloride (filtered through cotton)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1e53df174a954ad191326891a63848a3
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Reaction notes

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