Citric Acid → HCID 15379728, compound

HRID 2414722Notes

Reaction equation

HRID 2414722 reaction equation
[N:1]1([S:7](Cl)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]([C:21]([O:23][CH3:24])=[O:22])[NH:12]1.C(N1CCOCC1)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C([O-])(O)=O.[Na+]>C1COCC1.O.C(Cl)(Cl)Cl>[O:4]1[CH2:5][CH2:6][N:1]([S:7]([N:12]2[CH:13]([C:21]([O:23][CH3:24])=[O:22])[CH2:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11]2)(=[O:9])=[O:8])[CH2:2][CH2:3]1

Participants

9

Reactant 5

HCID 311Citric AcidHCID 7525EthylmorpholineHCID 516892Sodium BicarbonateHCID 4685119Methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylateHCID 12798265Morpholine-4-sulfonyl chloride

Product 1

HCID 15379728HCID 15379728, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

With stirring, 4.2 g (0.025 mol) of morpholine-N-sulfonyl chloride in 20 ml of THF are added dropwise to a solution of 4.8 g (0.025 mol) of methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate and 2.9 g (0.025 mol) of N-ethylmorpholine. The mixture is stirred at RT for 2 h and then heated under reflux for another 2 h so that the reaction goes to completion. CHCl3 is added to the reaction solution, which is then treated with 5% strength citric acid, 5% strength NaHCO3 solution and water. The organic phase is dried over Na2SO4 and evaporated to dryness. Yield of ester (26a): 7.5 g (92% of theory)

Workup

  1. stirringThe mixture is stirred at RT for 2 h
  2. temperatureheated
  3. temperatureunder reflux for another 2 h so that the reaction
  4. dry with materialThe organic phase is dried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-472f3adfcf794e95a473c14f82c37307
Source dataset
uspto-grants-2004_11
Patent number
US06815440B2

Reaction notes

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