HCID 22115821, compound → HCID 178480075, compound

HRID 1276201Notes

Reaction equation

HRID 1276201 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][C:7]([NH2:13])=[CH:8][CH:9]=2)[CH2:4]1.Cl.[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20](SCC)=[NH:21]>C(O)C>[ClH:1].[ClH:1].[CH3:2][N:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][C:7]([NH:13][C:20]([C:16]3[S:15][CH:19]=[CH:18][CH:17]=3)=[NH:21])=[CH:8][CH:9]=2)[CH2:4]1

Participants

4

Reactant 2

HCID 22115821HCID 22115821, compoundHCID 70131116Ethyl thiophene-2-carboximidothioate--hydrogen chloride (1/1)

Product 1

HCID 178480075HCID 178480075, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

2-Methyl-1,2,3,4-tetrahydroisoquinolin-7-ylamine hydrochloride (34.66 g) in 95% ethanol (600 ml) was warmed to 65° C. to dissolve most of the solids, and the mixture was then allowed to cool with stirring. The next day, the fine suspension of solids was treated with 2-thiophenecarboximidothioic acid, ethyl ester, hydrochloride (41 g) and stirred at 23° C. All solids had dissolved by 2 h, and by 4 h new solids had precipitated. The mixture was treated with concentrated hydrochloric acid (2 ml). The mixture was cooled to 0° C. and stirred for 30 minutes. The solids were filtered off, washed with ethanol (2×50 ml), and air dried to provide N-(2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-2-thiophenecarboximidamide dihydrochloride, m.p. 142-146° C.; MS m /z 272 [M+H]+.

Workup

  1. dissolutionto dissolve most of the solids
  2. temperatureto cool
  3. additionThe next day, the fine suspension of solids
  4. stirringstirred at 23° C
  5. dissolutionAll solids had dissolved by 2 h
  6. customby 4 h new solids had precipitated
  7. additionThe mixture was treated with concentrated hydrochloric acid (2 ml)
  8. stirringstirred for 30 minutes
  9. filtrationThe solids were filtered off
  10. washwashed with ethanol (2×50 ml), and air
  11. customdried

Sources & evidence

ORD record
ord-c085f190d14d4c0c8018d27c2595d44e
Source dataset
uspto-grants-2000_12
Patent number
US06166030

Reaction notes

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