Triethylamine → HCID 15917481, compound

HRID 1758530Notes

Reaction equation

HRID 1758530 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][C:7]3([O:17][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:10][NH:9][CH2:8]3.C(N(CC)CC)C.[C:27](Cl)(=[O:30])[CH2:28][CH3:29].CCCCCC.CCOCC>ClCCl>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][C:7]3([O:17][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:10][N:9]([C:27](=[O:30])[CH2:28][CH3:29])[CH2:8]3

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 15917441HCID 15917441, compoundHCID 21584099Diethylether hexane

Product 1

HCID 15917481HCID 15917481, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution of 6-chlorospiro[benzofuran-2(3H),4'(2'H)-isoquinoline] (6.0 g) and triethylamine (2.4 g) in dichloromethane (50 ml) is slowly added dropwise propionyl chloride (2.3 g) in dichloromethane (20 ml). The reaction mixture is stirred for 18 hours at ambient temperature, washed with water (2x), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvent is removed to yield an oil which, upon trituration with hexane/ether, yields product as a white solid (6.6 g, 92%). An analytical sample is recrystallized from hexane to yield a white solid, mp 106°-107°.

Workup

  1. washwashed with water (2x), saturated sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationAfter filtering
  4. customthe solvent is removed
  5. customto yield an oil which

Sources & evidence

ORD record
ord-e76d8f58256d4412a119248d0e72b913
Source dataset
uspto-grants-1983_02
Patent number
US04374137

Reaction notes

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