Triethylamine → HCID 15917481, compound

HRID 648105Notes

Reaction equation

HRID 648105 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-74b9e90e1e3b4c899c087c9c94ffcc05
Source dataset
uspto-grants-1983_10
Patent number
US04410699

Reaction notes

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