4-(2-Aminoethoxy)benzamide → 1-[2-(4-Carbamoylphenyloxy)-ethyl-amino]-3-(2-chloro-3-pyrazinyloxy)-2-propanol

HRID 1390663Notes

Reaction equation

HRID 1390663 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[CH:7][CH:6]=1.[Cl:14][C:15]1[C:20]([O:21][CH2:22][CH:23]2[O:25][CH2:24]2)=[N:19][CH:18]=[CH:17][N:16]=1>C(O)(C)C>[C:9]([C:8]1[CH:12]=[CH:13][C:5]([O:4][CH2:3][CH2:2][NH:1][CH2:24][CH:23]([OH:25])[CH2:22][O:21][C:20]2[C:15]([Cl:14])=[N:16][CH:17]=[CH:18][N:19]=2)=[CH:6][CH:7]=1)(=[O:10])[NH2:11]

Participants

4

Reactant 2

HCID 126663984-(2-Aminoethoxy)benzamideHCID 128021292-Chloro-3-(2,3-epoxy-propoxy)-pyrazine

Product 1

HCID 213331941-[2-(4-Carbamoylphenyloxy)-ethyl-amino]-3-(2-chloro-3-pyrazinyloxy)-2-propanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of 9.0 g of 4-(2-aminoethoxy)-benzamide in 120 ml of isopropanol is heated to the reflux temperature and a solution of 9.3 g of 2-chloro-3-(2,3-epoxy-propoxy)-pyrazine in 120 ml of isopropanol is added dropwise; duration of the addition: 5 hours. Thereafter the reaction mixture is heated to the reflux temperature for a further 7 hours. After completion of the reaction, the mixture is evaporated under a waterpump vacuum. The residue crystallises from ethyl acetate and gives 1-[2-(4-carbamoylphenyl-oxy)-ethyl-amino]-3-(2-chloro-3-pyrazinyloxy)-2-propanol, melting point 134°-135° C. after recrystallisation from isopropanol. The hydrochloride prepared therefrom using the calculated amount of methanolic hydrochloric acid melts at 223°-225° C. after crystallisation from a mixture of methanol and acetone.

Workup

  1. additionduration of the addition
  2. custom5 hours
  3. temperatureThereafter the reaction mixture is heated to the reflux temperature for a further 7 hours
  4. customAfter completion of the reaction
  5. customthe mixture is evaporated under a waterpump vacuum
  6. customThe residue crystallises from ethyl acetate

Sources & evidence

ORD record
ord-5ad022a5d5084afa91d44f9a0195c396
Source dataset
uspto-grants-1979_02
Patent number
US04139623

Reaction notes

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