2-Naphthylamine → HCID 86719466, compound

HRID 1772195Notes

Reaction equation

HRID 1772195 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH2:11].Cl.[Cl:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18]Cl>C(OCCOCCO)C.CO>[ClH:13].[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 70572-NaphthylamineHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 86719466HCID 86719466, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8146Diethylene Glycol Monoethyl EtherSolvent

Procedure

A solution of naphthalen-2-amine (2 g, 14 mmol) and bis(2-chloroethyl)amine hydrochloride (2.51 g, 14.1 mmol, 1 eq) in diethylene glycol monoethyl ether (3 mL) was stirred overnight at 149° C. (oil bath). The resulting solution was diluted with methanol (2 ml). The crude product was re-crystallized from diethyl ether to afford 1-(naphthalen-2-yl)piperazine hydrochloride as a yellow solid (2 g, 58%). (ES, m/z): [M+H]+ 213.0

Workup

  1. customThe crude product was re-crystallized from diethyl ether

Sources & evidence

ORD record
ord-da59ba815f05457ab6295070a470d7ea
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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