Hydrochloric Acid → 2-(5-Chloro-2-phenyl-1-benzothiophen-3-yl)-1-ethanamine Hydrochloride

HRID 2164140Notes

Reaction equation

HRID 2164140 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[S:6][C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:8]([CH2:9][C:10]#[N:11])[C:4]=2[CH:3]=1.[BH4-].[Na+].Cl>C(O)(C)C>[ClH:1].[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[S:6][C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:8]([CH2:9][CH2:10][NH2:11])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 4311764Sodium borohydrideHCID 219172462-(5-Chloro-2-phenyl-1-benzothiophen-3-yl)acetonitrile

Product 1

HCID 124121842-(5-Chloro-2-phenyl-1-benzothiophen-3-yl)-1-ethanamine Hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 6.9 parts by weight of 5-chloro-2-phenylbenzo[b]thiophene-3-acetonitrile in a solution of 11.6 parts by weight of cobaltous chloride hexahydrate in 300 parts by volume of methanol-benzene (5:1) is added, slowly, 9.2 parts by weight of sodium borohydride at 0° C. After the addition is completed, the mixture is allowed to warm to room temperature and then stirred for 19 hours. To the solution is now added 100 parts by volume of 3N hydrochloric acid. The solution is then stirred an additional 2 hours. The reaction mixture is 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, washed with brine, dried over magnesium sulfate and concentrated to afford crude 5-chloro-2-phenylbenzo[b]thiophene-3-ethaneamine as a yellow oil. This oil is dissolved in 15 parts by volume of isopropanol; to this solution is then added 8.0 parts by volume of isopropanolic/HCl. A solid precipitates out; 30 parts by volume of ethyl ether is now added and the mixture is stirred overnight. Removal by vacuum filtration of the resulting white solid material affords 5-chloro-2-phenylbenzo[b]thiophene-3-ethanamine hydrochloride, melting dec > 250° C. This compound is represented by the following structural formula ##STR19##

Workup

  1. additionis added
  2. customat 0° C
  3. additionAfter the addition
  4. stirringThe solution is then stirred an additional 2 hours
  5. customThe reaction mixture is partitioned between water and ether
  6. customThe aqueous layer is separated
  7. extractionextracted (3xs) with ether
  8. washwashed with brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customto afford crude 5-chloro-2-phenylbenzo[b]thiophene-3-ethaneamine as a yellow oil
  12. customA solid precipitates out
  13. addition30 parts by volume of ethyl ether is now added
  14. stirringthe mixture is stirred overnight
  15. customRemoval
  16. filtrationby vacuum filtration of the resulting white solid material

Sources & evidence

ORD record
ord-93bcb93a57c14575aed103b3b48631fc
Source dataset
uspto-grants-1979_01
Patent number
US04137414

Reaction notes

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