HCID 69449705, compound → HCID 11529099, compound

HRID 2060063Notes

Reaction equation

HRID 2060063 reaction equation
Cl.[CH3:2][N:3]([CH2:5][CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:15]C)[CH:12]=2)[C:7]1([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)O)[CH3:4]>Br.C(O)(=O)C>[CH3:4][N:3]([CH2:5][C:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:15])[CH:12]=2)[C:7]=1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH3:2]

Participants

4

Reactant 1

HCID 69449705HCID 69449705, compound

Product 1

HCID 11529099HCID 11529099, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Conditions

Temperature
105 °C

Procedure

0.84 g of 2-dimethylaminomethyl-5-methoxy-1-pyridin-3-yl-indan-1-ol hydrochloride (mixture of the diastereoisomers) was dissolved in about 13 ml of 33% hydrobromic acid in acetic acid and stirred for 3 hours under reflux at 100-110° C. The reaction mixture was concentrated in vacuo, rendered alkaline with 32% sodium hydroxide solution and extracted with ethyl acetate; the combined organic phases were dried over magnesium sulfate, stirred with activated carbon, filtered and concentrated. 0.62 g of 2-dimethylaminomethyl-1-pyridin-3-yl-3H-inden-5-ol was obtained and was dissolved in about 22 ml of 2-butanone/acetone (v/v=1:2) and converted into the corresponding hydrochloride with about 0.04 ml of water and about 0.58 ml of chlorotrimethylsilane, while cooling with ice; the hydrochloride was filtered off with suction, with the exclusion of air, washed with diisopropyl ether and dried in vacuo (about 50 mbar) (yield 0.631 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. stirringstirred with activated carbon
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-260aa46acd3540e5ab790d7f2c62f9cb
Source dataset
uspto-grants-2012_10
Patent number
US08278338B2

Reaction notes

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