Triethylamine → 2-(4-(4-Phenylbenzoylamino)butyl)-7-(3-pyridyl)sulfonyloxy-1,2,3,4-tetrahydroisoquinoline

HRID 1003710Notes

Reaction equation

HRID 1003710 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:30])[C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:20][CH:19]=3)[CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[N:38]1[CH:43]=[CH:42][CH:41]=[C:40]([S:44](Cl)(=[O:46])=[O:45])[CH:39]=1>ClCCl>[C:24]1([C:21]2[CH:20]=[CH:19][C:18]([C:17]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][N:8]3[CH2:7][CH2:6][C:5]4[C:10](=[CH:11][C:2]([O:1][S:44]([C:40]5[CH:39]=[N:38][CH:43]=[CH:42][CH:41]=5)(=[O:46])=[O:45])=[CH:3][CH:4]=4)[CH2:9]3)=[O:30])=[CH:23][CH:22]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3164136Pyridine-3-sulfonyl chlorideHCID 18797028HCID 18797028, compound

Product 1

HCID 187970042-(4-(4-Phenylbenzoylamino)butyl)-7-(3-pyridyl)sulfonyloxy-1,2,3,4-tetrahydroisoquinolineYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stored solution of 7-hydroxy-N-(4-(4-phenylbenzoylamino)butyl)-1,2,3,4-tetrahydroisoquinoline (05 g, 1.3 mmol) and triethylamine (0.21 ml; 1.5 mmol) in dichloromethane (20 ml) was added pyridine-3-sulfonyl chloride (0.25 g, 1.4 mmol). The mixture was stirred for 18 h, then partitioned between dichloromethane (4×30 ml) and saturated aqueous NaHCO3 (100 ml). Combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give an oil. Chromatography on silica using 0-5% methanolethyl acetate gradient elution gave the title compound (0.06 g, 12%) as an oil.

Workup

  1. custompartitioned between dichloromethane (4×30 ml) and saturated aqueous NaHCO3 (100 ml)
  2. dry with materialCombined organic extracts were dried (Na2SO4)
  3. customevaporated in vacuo
  4. customto give an oil
  5. washChromatography on silica using 0-5% methanolethyl acetate gradient elution

Sources & evidence

ORD record
ord-37ac9cbe112c435ebb53c8de3755e77c
Source dataset
uspto-grants-2000_04
Patent number
US06046210

Reaction notes

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