Acetonitrile → 2-Methyl-2,3-dihydro-5-benzo[b]furanyl-2-[4-(p-chlorophenyl)butylamino]-1-propanol

HRID 980503Notes

Reaction equation

HRID 980503 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[CH:4][CH:3]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].[BH4-].[Na+].[OH-:21].[Na+].[C:23](#N)[CH3:24]>O>[CH3:10][CH:9]1[O:21][C:4]2[CH:3]=[CH:2][C:7]([CH:13]([OH:16])[CH:23]([NH:12][CH2:11][CH2:10][CH2:9][CH2:8][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH3:24])=[CH:6][C:5]=2[CH2:8]1

Participants

7

Reactant 5

HCID 6342Acetonitrile2×HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 107738224-(4-Chlorophenyl)butan-1-amine

Product 1

HCID 137852402-Methyl-2,3-dihydro-5-benzo[b]furanyl-2-[4-(p-chlorophenyl)butylamino]-1-propanolYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8.2 gr. (45 moles) of p-chlorophenylbutylamine in 100 ml of acetonitrile is stirred and refluxed. 12.4 gr. (90 mmoles) of potassium carbonate are added thereto, then over one hour a solution of 12 gr. (45 mmoles) of the preceding brominated cetone in 80 ml of acetonitrile. After the end of the addition, reflux is maintained for 1.5 hour. To the medium at room temperature, a solution of 1.8 gr. (48 mmoles) of sodium borohydride in 10 ml of water basified with a drop of 40% aqueus NaOH is dropwise added. The solid is filtered and the filtrate is dry evaporated. The residue is a solid. The latter added to the first one is recrystallized from a 1:1 hexane/cyclohexane mixture. 5.1 gr. (14 mmoles, 31%) of a product are obtained, the melting point of which being 107.8° C. The NMR spectrum confirms the expected structure.

Workup

  1. temperaturerefluxed
  2. additionAfter the end of the addition
  3. temperaturereflux
  4. temperatureis maintained for 1.5 hour
  5. customat room temperature
  6. additionis dropwise added
  7. filtrationThe solid is filtered
  8. customthe filtrate is dry
  9. customevaporated
  10. additionThe latter added to the first one
  11. customis recrystallized from a 1:1 hexane/cyclohexane mixture

Sources & evidence

ORD record
ord-6d5798c34bdc48d6b2ca3a0191ca2d35
Source dataset
uspto-grants-1987_01
Patent number
US04638070

Reaction notes

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