Triethylamine → HCID 17866243, compound

HRID 1856796Notes

Reaction equation

HRID 1856796 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]([O:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])=[CH:11][CH:12]=2)[CH2:7]1.[N+:24]([C:27]1[CH:37]=[CH:36][C:30](/[CH:31]=[CH:32]/[C:33](Cl)=[O:34])=[CH:29][CH:28]=1)([O-:26])=[O:25].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[N+:24]([C:27]1[CH:28]=[CH:29][C:30](/[CH:31]=[CH:32]/[C:33]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][C:10]([O:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])=[CH:11][CH:12]=3)[CH2:7]2)=[O:34])=[CH:36][CH:37]=1)([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 5971362trans-4-Nitrocinnamoyl chlorideHCID 22132518HCID 22132518, compound

Product 1

HCID 17866243HCID 17866243, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(4-aminobutyl)-7-trifluoromethylsulfonyloxy-1,2,3,4-tetrahydroisoquinoline (400 mg, 1.14 mmol), trans-4-nitrocinnamoyl chloride (240 mg, 1.14 mmol) and triethylamine (0.2 ml, 1.37 mmol) in dichloromethane (6 ml) was shaken at room temperature for 18 h. Saturated aqueous potassium carbonate (5 ml) was added and shaking resumed for 15 mins. The organic layer was chromatographed on silica using 10-100% ethyl acetate-hexane gradient elution to afford the title compound as a yellow gum (490 mg, 82%).

Workup

  1. stirringshaking
  2. waitresumed for 15 mins
  3. customThe organic layer was chromatographed on silica using 10-100% ethyl acetate-hexane gradient elution

Sources & evidence

ORD record
ord-73d1fc6226b0418783528241e1bef5e8
Source dataset
uspto-grants-2000_11
Patent number
US06143762

Reaction notes

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