Formaldehyde → 7-Bromo-2-dimethylaminomethyl-1-tetralone hydrochloride

HRID 2413264Notes

Reaction equation

HRID 2413264 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[ClH:13].[CH3:14][NH:15][CH3:16].[CH2:17]=O>Cl.C(O)C>[ClH:13].[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:14][N:15]([CH3:17])[CH3:16])[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 233209337-Bromo-2-dimethylaminomethyl-1-tetralone hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-bromo-1-tetralone (4.50 g), dimethylamine hydrochloride (2.50 g), paraformaldehyde (1.0 g), ethanol (6 ml) and concentrated hydrochloric acid (4 drops) was heated under reflux for two hours and cooled. The mixture was diluted with a few ml. of acetone and the solid was filtered off, washed with a little acetone and dried to give 7-bromo-2-dimethylaminomethyl-1-tetralone hydrochloride, m.p. 169°-171°, pure enough for further reaction.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for two hours
  3. temperaturecooled
  4. additionThe mixture was diluted with a few ml
  5. filtrationof acetone and the solid was filtered off
  6. washwashed with a little acetone
  7. customdried

Sources & evidence

ORD record
ord-51f045b541964c298852d3873cb3fc6d
Source dataset
uspto-grants-1985_01
Patent number
US04496572

Reaction notes

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