Triethylamine → 5-[1-Hydroxy-2-(4-(4-methyl-2-thiazolyl)-piperazino)-ethyl]salicylamide

HRID 704316Notes

Reaction equation

HRID 704316 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[S:5][CH:6]=1.Br[CH2:14][CH:15]([C:17]1[CH:25]=[C:21]([C:22]([NH2:24])=[O:23])[C:20]([OH:26])=[CH:19][CH:18]=1)[OH:16].C(N(CC)CC)C>CCOCC>[OH:16][CH:15]([C:17]1[CH:25]=[C:21]([C:22]([NH2:24])=[O:23])[C:20]([OH:26])=[CH:19][CH:18]=1)[CH2:14][N:10]1[CH2:11][CH2:12][N:7]([C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]=2)[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 144798721-(4-Methyl-1,3-thiazol-2-yl)piperazineHCID 144798735-(2-Bromo-1-hydroxyethyl)-salicylamide

Product 1

HCID 144798745-[1-Hydroxy-2-(4-(4-methyl-2-thiazolyl)-piperazino)-ethyl]salicylamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

18.9 g of 1-(4-methyl-2-thiazolyl)-piperazine and 26 g of 5-(2-bromo-1-hydroxyethyl)-salicylamide (obtainable by acylation of salicyamide with bromoacetyl bromide/AlCl3 to give 5-bromoacetyl-salicylamide and subsequent reaction with NaBH4) are dissolved in 400 ml of ether, 15 ml of triethylamine are added, the mixture is boiled for 2 h and subjected to the usual working-up, and 5-[1-hydroxy-2-(4-(4-methyl-2-thiazolyl)-piperazino)-ethyl]salicylamide ("A"), m.p. 182°, is obtained. Dihydrochloride m.p. 244°-245°.

Sources & evidence

ORD record
ord-36b26afb54da46fb8c339c8f6342a94e
Source dataset
uspto-grants-1991_01
Patent number
US04987133

Reaction notes

Loading…