2-((4-(2-(Cyclopropylmethoxy)ethyl)phenoxy)methyl)oxirane → 1-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-benzylamino]-3-[4-[2-(cyclopropylmethoxy)ethyl]-phenoxy]-2-propanol

HRID 4555

Reaction equation

HRID 4555 reaction equation
[CH:1]1([CH2:4][O:5][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]3[O:18][CH2:17]3)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[CH2:19]([NH:26][CH:27](C)[CH2:28][O:29][C:30]1[CH:38]=[C:34]([C:35]([NH2:37])=[O:36])[C:33]([OH:39])=[CH:32][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)(C)C>[C:35]([C:34]1[CH:38]=[C:30]([CH:31]=[CH:32][C:33]=1[OH:39])[O:29][CH2:28][CH2:27][N:26]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:17][CH:16]([OH:18])[CH2:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][O:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)=[CH:13][CH:12]=1)(=[O:36])[NH2:37]

Participants

4

Reactant 2

HCID 117915422-((4-(2-(Cyclopropylmethoxy)ethyl)phenoxy)methyl)oxiraneHCID 137543345-(2-Benzylaminopropoxy)salicylamide

Product 1

HCID 201513211-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-benzylamino]-3-[4-[2-(cyclopropylmethoxy)ethyl]-phenoxy]-2-propanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 14.3 g of 1-[2-(cyclopropyl-methoxy)ethyl]-4-(2,3-epoxypropoxy)-benzene (German Offenlegungsschrift No. 2,649,605) and 16.3 g of 5-[2-(benzylamino)propoxy]-salicylamide in 200 ml of isopropanol is refluxed for 18 hours. The reaction mixture is concentrated by evaporation to leave crude 1-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-benzylamino]-3-[4-[2-(cyclopropylmethoxy)ethyl]-phenoxy]-2-propanol in the form of brown oil, which can be further processed without additional purification.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation

Sources & evidence

ORD record
ord-b95195d2cd784a148d1234c8bc6ee701
Source dataset
uspto-grants-1988_02
Patent number
US04727067

Linked notes

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