N,N-Bis(2-chloroethyl)-2-methoxyaniline → 1,2,3,4-Tetrahydro-6-hydroxy-2-[4-(2-methoxyphenyl)-1-piperazinyl]-naphthalene

HRID 1660488Notes

Reaction equation

HRID 1660488 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:13][CH2:14]Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12].[NH2:16][CH:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([OH:27])[CH:23]=2)[CH2:18]1>C(O)C>[OH:27][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[CH2:18][CH:17]([N:16]1[CH2:14][CH2:13][N:4]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[O:11][CH3:12])[CH2:3][CH2:2]1)[CH2:26][CH2:25]2

Participants

4

Reactant 2

HCID 227137N,N-Bis(2-chloroethyl)-2-methoxyanilineHCID 131778796-Amino-5,6,7,8-tetrahydronaphthalen-2-ol

Product 1

HCID 205568141,2,3,4-Tetrahydro-6-hydroxy-2-[4-(2-methoxyphenyl)-1-piperazinyl]-naphthalene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.48 g of N,N-Di(2-chloroethyl)-2-methoxyaniline are dissolved together with 1.63 g of 2-amino-1,2,3,4-tetrahydro-6-hydroxynaphthalene in 100 ml of ethanol and finally refluxed for 20 hours. The solvent is evaporated off and the residue recrystallized from methanol/ether to yield the title compound. M.P. 282°-286° [Hydrochloride salt form].

Workup

  1. temperaturefinally refluxed for 20 hours
  2. customThe solvent is evaporated off
  3. customthe residue recrystallized from methanol/ether

Sources & evidence

ORD record
ord-cae9cf9f7e7c4e7684699a47f1e0a275
Source dataset
uspto-grants-1981_12
Patent number
US04308266

Reaction notes

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