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

HRID 280627Notes

Reaction equation

HRID 280627 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-d3d0fbaff7b24b45bce90989ea617b9a
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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