Hydrochloric Acid → HCID 20287077, compound

HRID 127473

Reaction equation

HRID 127473 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:15])=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:4].[CH3:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(N(CC)CC)C.Br.C(N(CC)CC)C.[ClH:44]>O1CCCC1.C(OCC)C>[ClH:44].[ClH:44].[OH:15][C:8]1[CH:7]=[CH:6][C:5]([C:3](=[O:4])[CH2:2][N:26]2[CH2:27][CH2:28][N:23]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH3:16])[CH2:24][CH2:25]2)=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 919652-MeppHCID 2734074Triethylammonium bromideHCID 11601501Methyl 5-(2-bromoacetyl)-2-hydroxybenzoate

Product 1

HCID 20287077HCID 20287077, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 10.9 g (0.04 mol) of methyl 5-(2-bromoacetyl)-2-hydroxybenzoate in 100 ml of dry tetrahydrofuran is added dropwise over 4 hours to a stirred solution of 7.1 g (0.04 mol) of 1-(2-methylphenyl)piperazine and 4.0 g (0.04 mol) of triethylamine in 75 ml of tetrahydrofuran at room temperature. Stirring is continued for 2-12 hours or until the theoretical amount (7.3 g) of triethylamine hydrobromide precipitates. The precipitates is removed by filtration and the filtrate is evaporated to dryness. Addition of 2 equivalents of methanolic HCl and precipitation by addition of ethyl ether at room temperature affords the crude methyl 2-hydroxy-5-[2-[4-(2-methylphenyl)-1-piperazinyl]acetyl]benzoate dihydrochloride (9.4 g). Attempts to purify this product by recrystallization frequently led to decomposition and were subsequently avoided.

Workup

  1. customprecipitates
  2. customThe precipitates is removed by filtration
  3. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-35f46730076441c895e1fb9d05cddd04
Source dataset
uspto-grants-1981_03
Patent number
US04255575

Linked notes

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