Butylamine → HCID 19955581, compound

HRID 1779445Notes

Reaction equation

HRID 1779445 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[I:15])=[CH:5][CH:4]=1.[CH2:16]([NH2:20])[CH2:17][CH2:18][CH3:19]>O1CCCC1>[I:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH:20][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 8007ButylamineHCID 19955577HCID 19955577, compound

Product 1

HCID 19955581HCID 19955581, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromomethyl-2'-iodobiphenyl (4.0 g; preparable as in Example 2(b)) and butylamine (40 ml) in dry tetrahydrofuran (55 ml) was stirred for 18 hours an ambient temperature then boiled under reflux for 45 minutes. The solvent was evaporated under reduced pressure and the resulting residue was then dissolved in dichloromethane (100 ml) to give a solution which was washed with aqueous potassium hydroxide solution (1M; 2×50 ml), water (50 ml), then hydrochloric acid (5M; 2×50 ml), then organic layer was dried over magnesium sulphate and the organic solvent was evaporated. The residue obtained was purified by flash chromatography on silica gel (eluting with dichloromethane/methanol (9:1) to give the intermediate compound N-(2'-iodobiphenyl-4ylmethyl)butylamine (1.9 g; m.p. 134°-136° C.).

Workup

  1. temperatureunder reflux for 45 minutes
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe resulting residue was then dissolved in dichloromethane (100 ml)
  4. customto give a solution which
  5. washwas washed with aqueous potassium hydroxide solution (1M; 2×50 ml), water (50 ml)
  6. dry with materialhydrochloric acid (5M; 2×50 ml), then organic layer was dried over magnesium sulphate
  7. customthe organic solvent was evaporated
  8. customThe residue obtained
  9. customwas purified by flash chromatography on silica gel (
  10. washeluting with dichloromethane/methanol (9:1)

Sources & evidence

ORD record
ord-6e94ffe208ba41dfad95c8203146aa92
Source dataset
uspto-grants-1997_05
Patent number
US05627191

Reaction notes

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