Hydrochloric Acid → Thieno(3,2-c)pyridine, 4,5,6,7-tetrahydro-5-((2-methylphenyl)methyl)-, monohydrochloride

HRID 1638152Notes

Reaction equation

HRID 1638152 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][NH:6][CH2:7][CH2:8][C:9]1[S:10][CH:11]=[CH:12][CH:13]=1.Cl.O1CCO[CH2:20]1>>[ClH:1].[CH3:2][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:7][CH2:8][C:9]2[S:10][CH:11]=[CH:12][C:13]=2[CH2:20]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 125861,3-DioxolaneHCID 70270911HCID 70270911, compound

Product 1

HCID 3041292Thieno(3,2-c)pyridine, 4,5,6,7-tetrahydro-5-((2-methylphenyl)methyl)-, monohydrochlorideYield 62.7%

Conditions

Temperature
10 °C

Procedure

N-[(2-methylbenzyl)]-2-(2-thienyl)ethylamine HCl (26.8 g, 0.1 moles) is suspended in 75 ml of 1,3-dioxolane. 0.25 ml of 37% hydrochloride acid is added. The reaction mixture is refluxed for 24 hours. Thereafter, the mixture is cooled to 10° C. and the crystalline precipitate is filtered and washed twice with 5 ml of isopropanol. The product is dried at 60° C. under vacuum to yield 17.4 g (62.7%) of 5-(2-methylbenzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine HCl having a m.p. of 207-210° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 24 hours
  2. filtrationthe crystalline precipitate is filtered
  3. washwashed twice with 5 ml of isopropanol
  4. customThe product is dried at 60° C. under vacuum

Sources & evidence

ORD record
ord-481a327591ba4fd1a501ca4b119c5418
Source dataset
uspto-grants-2000_03
Patent number
US06043368

Reaction notes

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