Hydrochloric Acid → HCID 12412186, compound

HRID 2164141Notes

Reaction equation

HRID 2164141 reaction equation
[C:1]1([C:7]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]=2[CH2:16][C:17]#[N:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].[ClH:21]>C(Cl)(Cl)Cl>[ClH:21].[C:1]1([C:7]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]=2[CH2:16][CH2:17][NH2:18])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22750359HCID 22750359, compound

Product 1

HCID 12412186HCID 12412186, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 15.5 parts by weight of 2-phenylbenzo[b]thiophene-3-acetonitrile in a solution of 29.6 parts by weight of cobaltous chloride hexahydrate in 769 parts by volume of methanol-benzene (5:1) is added slowly 23.8 parts by weight of sodium borohydride at 0° C. After the addition is completed, the mixture is allowed to warm to room temperature and stirred for 72 hours. The reaction mixture is then partitioned between water and ether. The aqueous layer is separated, basified with concentrated ammonium hydroxide and extracted (3xs) with ether. The organic fractions are combined, dried and concentrated to afford crude 2-phenylbenzo[b]thiophene-3-ethanamine. This material is dissolved in chloroform and shaken with 100 parts by volume of 10% aqueous hydrochloric acid. A solid precipitates; filtration of this material affords 2-phenylbenzo[b]thiophene-3-ethanamine hydrochloride, melting at 200°-201° C. (decomposition). This compound is represented by the following stuctural formula. ##STR28##

Workup

  1. additionAfter the addition
  2. customThe reaction mixture is then partitioned between water and ether
  3. customThe aqueous layer is separated
  4. extractionextracted (3xs) with ether
  5. customdried
  6. concentrationconcentrated
  7. customto afford crude 2-phenylbenzo[b]thiophene-3-ethanamine
  8. customA solid precipitates
  9. filtrationfiltration of this material

Sources & evidence

ORD record
ord-c77c21e7d4b24732b998bb93c1d16fb7
Source dataset
uspto-grants-1979_01
Patent number
US04137414

Reaction notes

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