Water → HCID 178456192, compound

HRID 1276202Notes

Reaction equation

HRID 1276202 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)=[NH:13])[CH:9]=2)[CH2:4][CH2:3][NH:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:26]([CH3:28])[CH3:27].O>CN(C)C=O.C1CCCCC1.C(OCC)(=O)C>[CH:26]([N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][C:8]([NH:11][C:12]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)=[NH:13])=[CH:7][CH:6]=2)[CH2:1]1)([CH3:28])[CH3:27]

Participants

8

Reactant 4

HCID 962WaterHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 178511886HCID 178511886, compound

Product 1

HCID 178456192HCID 178456192, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of N-(1,2,3,4-tetrahydroisoquinolin-7-yl)-2-thiophenecarboximidamide (7.0 g, 21 mmol) in dimethylformamide (100 ml) was added potassium carbonate (14.6 g, 100 mmol). To this mixture was added 2-bromopropane (5.1 g, 42 mmol), and the mixture was then heated to 40° C. for 72 h. The reaction mixture was poured into water (500 ml) and extracted with ethyl acetate (3×100 ml). The combined ethyl acetate extracts were washed with water (200 ml) and dried over magnesium sulfate. Evaporation of the solvent yielded a crude oil, which was then dissolved in hot cyclohexane (250 ml) and ethyl acetate (10 ml). Upon standing the title compound crystallized out and was collected by filtration (3.2 g), m.p. 110-111° C.

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washThe combined ethyl acetate extracts were washed with water (200 ml)
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent
  5. customyielded a crude oil, which

Sources & evidence

ORD record
ord-f793bbab7bf04345a547a9532dd9da90
Source dataset
uspto-grants-2000_12
Patent number
US06166030

Reaction notes

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