7-Methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid → n-(4-Bromophenyl)-n-[(4-dimethylaminophenyl)methyl]-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxamide hydrochloride

HRID 218697Notes

Reaction equation

HRID 218697 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]2[C:13]([OH:15])=O)=[CH:5][CH:4]=1.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=2)=[CH:19][CH:18]=1.[ClH:34].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:34].[Br:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([N:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=2)[C:13]([CH:10]2[C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[CH2:7][CH2:8][CH2:9]2)=[O:15])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 132774847-Methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acidHCID 151741014-[(4-Bromoanilino)methyl]-N,N-dimethylanilineHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 67183700n-(4-Bromophenyl)-n-[(4-dimethylaminophenyl)methyl]-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

7-Methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (0.47 g) and (4-bromophenyl)[(4-dimethylaminophenyl)methyl]-amine (0.70 g) as starting materials were reacted and treated in the same manner as in Example 12. The obtained solid was dissolved in ethyl acetate (4 mL). Thereto was added 4 mol/L-HCl/ethyl acetate (0.35 mL), and the precipitated solid was collected by filtration to give N-(4-bromophenyl)-N-[(4-dimethylaminophenyl)methyl]-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxamide hydrochloride (0.65 g). melting point: 104-113° C.

Workup

  1. customwere reacted
  2. additiontreated in the same manner as in Example 12
  3. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-92aff4c098a6411f8a1fb049fefe2157
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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