Phosphoric Acid → 5-BroModescyano CitalopraM

HRID 2414463Notes

Reaction equation

HRID 2414463 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH2:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])[OH:9])=[C:4]([CH2:23]O)[CH:3]=1.P(=O)(O)(O)O>>[CH3:15][N:13]([CH2:12][CH2:11][CH2:10][C:8]1([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[O:9][CH2:23][C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]1=2)[CH3:14]

Participants

3

Reactant 2

HCID 1004Phosphoric AcidHCID 10172919HCID 10172919, compound

Product 1

HCID 101504575-BroModescyano CitalopraMYield 85.1%

Procedure

The (4-bromo-2-(hydroxymethyl)phenyl)-(4′fluorophenyl)-(3-dimethylamino-propyl)methanol residue (160 g) was heated with 50% aqueous phosphoric acid (1.99 kg) with vigorous stirring. The reaction mass was purified by extraction and neutralized with aqueous ammonia at a temperature below 30° C. The reaction mass was extracted with toluene and the solvent distilled under reduced pressure to give 1-(4′fluorophenyl)-1-(3-dimethylaminopropyl)-5-bromophthalane (130 g).

Workup

  1. customThe reaction mass was purified by extraction
  2. customneutralized with aqueous ammonia at a temperature below 30° C
  3. extractionThe reaction mass was extracted with toluene
  4. distillationthe solvent distilled under reduced pressure

Sources & evidence

ORD record
ord-25eccd49faf34dce985e6b820f4c675f
Source dataset
uspto-grants-2004_11
Patent number
US06812355B2

Reaction notes

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