Hydrochloric Acid → HCID 66755777, compound

HRID 1642115Notes

Reaction equation

HRID 1642115 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][NH:6]1.C(N(CC)CC)C.[Cl:23][C:24]1[CH:25]=[C:26]([S:31](Cl)(=[O:33])=[O:32])[CH:27]=[CH:28][C:29]=1[Cl:30].Cl>C(Cl)Cl>[Cl:23][C:24]1[CH:25]=[C:26]([S:31]([N:6]2[CH2:7][CH2:8][C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:5]2[CH2:4][C:3]([O:2][CH3:1])=[O:15])(=[O:32])=[O:33])[CH:27]=[CH:28][C:29]=1[Cl:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 8471TriethylamineHCID 45588337Methyl (1,2,3,4-tetrahydroisoquinolin-1-yl)acetate

Product 1

HCID 66755777HCID 66755777, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2-(1,2,3,4-Tetrahydroisoquinolin-1-yl)acetic acid methyl ester (7.49 g, 36.5 mmol) was dissolved in DCM (200 ml), and triethylamine (11.7 ml, 83 mmol) was added thereto. The reaction solution was cooled to 0° C., and a solution of 3,4-dichlorobenzenesulfonyl chloride (8.14 g, 33.2 mmol) in DCM (100 ml) was added dropwise. After 3 h, 0.5 M HCl (100 ml) was added. After phase separation, the organic phase was washed with water, dried (sodium sulfate) and concentrated. Purification was carried out by column chromatography on silica gel (heptane/ethyl acetate 4:1).

Workup

  1. customAfter phase separation
  2. washthe organic phase was washed with water
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. customPurification

Sources & evidence

ORD record
ord-b8234c9624f441e8bde4a6b88b4a8108
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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