Hydrochloric Acid → HCID 54243229, compound

HRID 728265Notes

Reaction equation

HRID 728265 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:13]#[N:14])[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:16][CH2:17][CH2:18][C:19]1[O:20][C:21]([CH3:24])=[CH:22][CH:23]=1.[Mg].[BH4-].[Na+].Cl>CCOCC.CC(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH:13]([NH2:14])[CH2:16][CH2:17][CH2:18][C:19]3[O:20][C:21]([CH3:24])=[CH:22][CH:23]=3)[CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 5462224MagnesiumHCID 108571341-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrileHCID 1578219728333-61-1

Product 1

HCID 54243229HCID 54243229, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

1-(3,4-Dichlorophenyl)cyclobutanecarbonitrile (8 g) was added to the Grignard reagent prepared by the reaction under argon of 2-(3-bromopropyl)-5-methylfuran (10 g) and magnesium (1.1 g) in ether (20 ml). The mixture was stirred for 16 hours at ambient temperature. A suspension of sodium borohydride (3 g) in propan-2-ol (100 ml) was added and the mixture heated under reflux for 4.75 hours and then allowed to cool. The mixture was added to water with cooling and excess 2N hydrochloric acid added. The aqueous acid layer was extracted with ether and the extract washed with 1N aqueous sodium hydroxide solution, dried and evaporated to yield 1-[1-(3,4-dichlorophenyl)cyclobutyl]-4-(5-methyl-2-furyl)butylamine.

Workup

  1. additionwas added
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 4.75 hours
  4. temperatureto cool
  5. temperaturewith cooling
  6. extractionThe aqueous acid layer was extracted with ether
  7. washthe extract washed with 1N aqueous sodium hydroxide solution
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-61c37339ffe74bc0bc9c11fe5ffc348c
Source dataset
uspto-grants-1991_09
Patent number
US05047432

Reaction notes

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