Methylamine → N-methyl-1,2,3,4-tetrahydroisoquinoline-7-carboxamide

HRID 1713091Notes

Reaction equation

HRID 1713091 reaction equation
Cl.C[O:3][C:4]([C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][NH:12][CH2:13]2)=[CH:8][CH:7]=1)=O.[CH3:16][NH2:17]>>[CH3:16][NH:17][C:4]([C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][NH:12][CH2:13]2)=[CH:8][CH:7]=1)=[O:3]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 44607839Methyl 1,2,3,4-tetrahydroisoquinoline-7-carboxylate hydrochloride

Product 1

HCID 57479413N-methyl-1,2,3,4-tetrahydroisoquinoline-7-carboxamide

Conditions

Temperature
100 °C

Procedure

1,2,3,4-Tetrahydro-isoquinoline-7-carboxylic acid methyl ester hydrochloride (113 mg, 0.5 mmol) is dissolved in aqueous methylamine (40%, 5.0 ml)) and heated at 100° C. overnight. Upon cooling to rt, the reaction mixture is evaporated to dryness under reduced pressure. The residue is taken up in water (1.0 ml), and treated with sodium hydroxide solution (1.0 N, 1.0 ml). The mixture is extracted with DCM (10 ml×3). The combined organic phase is dried over sodium sulfate, and concentrated to give the title compound. MS (+VE) m/z 191.1 (M++1).

Workup

  1. temperatureUpon cooling to rt
  2. customthe reaction mixture is evaporated to dryness under reduced pressure
  3. additiontreated with sodium hydroxide solution (1.0 N, 1.0 ml)
  4. extractionThe mixture is extracted with DCM (10 ml×3)
  5. dry with materialThe combined organic phase is dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-22de711e3d0f49359efdeda1803ff613
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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