Acetonitrile → HCID 86700708, compound

HRID 530457Notes

Reaction equation

HRID 530457 reaction equation
Br[CH2:2][CH2:3][CH2:4]O.[C:6]([O-:9])([O-])=O.[K+].[K+].[CH3:12][S:13](Cl)(=[O:15])=[O:14].[CH3:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21].[CH3:24][C:25]#N>C(Cl)Cl>[CH3:12][S:13]([O:9][CH2:6][CH2:17][CH2:18][N:19]1[CH2:22][CH2:23][C:25]2[C:21](=[CH:2][CH:3]=[CH:4][CH:24]=2)[CH2:20]1)(=[O:15])=[O:14]

Participants

7

Reactant 5

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 31297Methanesulfonyl chloride

Product 1

HCID 86700708HCID 86700708, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

3-Bromo-1-propanol (100 mg, 0.72 mmol), K2CO3 (249 mg, 1.80 mmol) and 1,2,3,4-tetrahydrisoquinoline (95.8 mg, 0.72 mmol) were dissolved in MeCN (2 mL) and the reaction mixture was heated at 60° C. for 18 h. The reaction mixture was filtered and concentrated in vacuo. The residue was dissolved in DCM (10 mL) and methanesulphonyl chloride (82.4 mg, 0.72 mmol) and Et3N (87.4 mg, 0.86 mmol) were added. The reaction mixture was stirred for 1 h, diluted with DCM (20 mL), washed with sat aq NaHCO3 (20 mL), dried (MgSO4) and concentrated in vacuo to give the crude title compound (72.2 mg) as a colourless gum. LCMS (ES+): 270.3 [MH]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in DCM (10 mL)
  4. washwashed
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d4d391eef9b4b808e390dc269748213
Source dataset
uspto-grants-2016_05
Patent number
US09353086B2

Reaction notes

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