Dimethylamine → 5-Bromo-2,3-dihydro-N,N-dimethyl-1H-inden-1-amine

HRID 896072Notes

Reaction equation

HRID 896072 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7](Cl)[CH2:6][CH2:5]2.[CH3:12][NH:13][CH3:14]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([N:13]([CH3:14])[CH3:12])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 674DimethylamineHCID 223495155-Bromo-1-chloro-2,3-dihydro-1H-indene

Product 1

HCID 223495485-Bromo-2,3-dihydro-N,N-dimethyl-1H-inden-1-amineYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-bromo-1-chloro-indane (542 mg, 2.35 mmol) in toluene (9 ml) was added dimethylamine (3 ml) and resulting mixture was heated at 90° C. for 1.5 hr. The reaction mixture is concentrated under reduced pressure to yield the title compound (300 mg, 53%). 1H NMR (CDCl3): 2.06 (m, 2H), 2.24 (s, 6H), 2.81-2.93 (m, 2H), 4.27 (t, 1H), 7.22 (d, 1H), 7.33 (d 1H), 7.36 (s, 1H).

Workup

  1. customresulting mixture
  2. concentrationThe reaction mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-6812c9fe88d24300b655f476ca265438
Source dataset
uspto-grants-2005_07
Patent number
US06919335B2

Reaction notes

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