Hydrochloric Acid → HCID 70577300, compound

HRID 127476Notes

Reaction equation

HRID 127476 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([O:15][CH3:16])=[C:9]([CH:14]=1)[C:10]([O:12]C)=[O:11])=[O:4].[C:17]1([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.[ClH:36]>O1CCCC1.C(OCC)C>[ClH:36].[CH3:16][O: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:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:24][CH2:25]2)=[CH:14][C:9]=1[C:10]([OH:12])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 20287115Methyl 5-(2-bromoacetyl)-2-methoxybenzoate

Product 1

HCID 70577300HCID 70577300, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 15.0 g (0.0522 mol) of methyl 5-(bromoacetyl)-2-methoxybenzoate in 500 ml of anhydrous tetrahydrofuran is added dropwise over 2-4 hours to a solution of 8.48 g (0.0522 mol) of 1-phenylpiperazine and 5.28 g (0.0522 mol) of triethylamine in 100 ml of tetrahydrofuran. The mixture is stirred at room temperature under exclusion of moisture overnight. The precipitated triethylamine hydrobromide 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 yields crude 2-methoxy-5-[2-(4-phenyl-1-piperazinyl)acetyl]benzoate hydrochloride (21.0 g) that can be used without further purification.

Workup

  1. customThe precipitated triethylamine hydrobromide is removed by filtration
  2. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-20df5092cd8c4ca4b059ecb54e751e9f
Source dataset
uspto-grants-1981_03
Patent number
US04255575

Reaction notes

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