1-Phenethylamine → HCID 13649325, compound

HRID 1200149Notes

Reaction equation

HRID 1200149 reaction equation
ClC(OCC(C)C)=O.[Cl:9][C:10]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:11]=1[C:12]([NH:14][CH2:15][C:16]([OH:18])=O)=[O:13].C(N(CC)CC)C.[C:31]1([CH:37]([NH2:39])[CH3:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1>[CH3:38][CH:37]([NH:39][C:16](=[O:18])[CH2:15][NH:14][C:12](=[O:13])[C:11]1[C:19]([Cl:23])=[CH:20][CH:21]=[CH:22][C:10]=1[Cl:9])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 74081-PhenethylamineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 14696313HCID 14696313, compound

Product 1

HCID 13649325HCID 13649325, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.05 g of isobutyl chloroformate was slowly dropped at -20° C. under a nitrogen stream onto a solution of 1.74 g of N-(2,6-dichlorobenzoyl)glycine and 0.71 g of triethylamine in 30 ml of anhydrous tetrahydrofuran, and the reaction solution was stirred for 20 minutes. Then, 0.84 g of α-phenylethylamine was added to the solution, which was subsequently stirred for 30 minutes keeping the reaction temperature within the range from -10° C. to -20° C. The reaction solution was then extracted with 60 ml of ethyl acetate. The extract was washed with a 10% w/v aqueous solution of sodium hydroxide, then with 1N aqueous hydrochloric acid, and finally with a saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate. The reaction solution was concentrated by evaporation under reduced pressure, and the resulting residue was subjected to silica gel column chromatography for purification to give 1.58 g (yield 67%) of the title product melting at 155° C.

Workup

  1. stirringwas subsequently stirred for 30 minutes
  2. customfrom -10° C. to -20° C
  3. extractionThe reaction solution was then extracted with 60 ml of ethyl acetate
  4. washThe extract was washed with a 10% w/v aqueous solution of sodium hydroxide
  5. dry with materialwith 1N aqueous hydrochloric acid, and finally with a saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate
  6. concentrationThe reaction solution was concentrated by evaporation under reduced pressure
  7. customthe resulting residue was subjected to silica gel column chromatography for purification

Sources & evidence

ORD record
ord-951bdd371ab9424aac0ec8374ab131af
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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