Triethylamine → HCID 22132526, compound

HRID 1856785Notes

Reaction equation

HRID 1856785 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][N:16]3[C:20](=[O:21])[C:19]4=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]4[C:17]3=[O:26])[CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:34]1[CH:38]=[CH:37][CH:36]=[C:35]1[S:39](Cl)(=[O:41])=[O:40]>ClCCl>[C:20]1(=[O:21])[N:16]([CH2:15][CH2:14][CH2:13][CH2:12][N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:2]([O:1][S:39]([C:35]4[S:34][CH:38]=[CH:37][CH:36]=4)(=[O:41])=[O:40])=[CH:3][CH:4]=3)[CH2:9]2)[C:17](=[O:26])[C:18]2=[CH:25][CH:24]=[CH:23][CH:22]=[C:19]12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 22132507HCID 22132507, compound

Product 1

HCID 22132526HCID 22132526, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 7-hydroxy-2-(4-phthalimidobutyl)-1,2,3,4-tetrahydroisoquinoline (2.94 g, 8.4 mmol) and triethylamine (1.4 ml, 10 mmol) in dichloromethane (75 ml) was treated with 2-thiophenesulfonyl chloride (1.69 g, 9.2 mmol). After stirring at room temperature for 18 h the mixture was washed with saturated aqueous sodium bicarbonate (100 ml). The aqueous layer was separated and extracted with dichloromethane (2×50 ml). The combined extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica using 30-100% ethyl acetate-pentane gradient elution to afford the title compound as a pale yellow oil (3.45 g, 83%).

Workup

  1. washwas washed with saturated aqueous sodium bicarbonate (100 ml)
  2. customThe aqueous layer was separated
  3. extractionextracted with dichloromethane (2×50 ml)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica using 30-100% ethyl acetate-pentane gradient elution

Sources & evidence

ORD record
ord-edca271eafdf417ebfc415ae5192da6c
Source dataset
uspto-grants-2000_11
Patent number
US06143762

Reaction notes

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