Ammonia → Mirtazapine

HRID 1369131Notes

Reaction equation

HRID 1369131 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]([C:14]2[N:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20]O)[CH2:4][CH2:3]1.S(=O)(=O)(O)O.N.[OH-].[Na+]>>[CH3:1][N:2]1[CH2:7][CH:6]2[N:5]([C:14]3[N:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH2:20][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=32)[CH2:4][CH2:3]1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 102214352-(4-Methyl-2-phenyl-1-piperazinyl)-3-pyridinemethanol

Product 1

HCID 4205MirtazapineYield 95%

Procedure

1-(3-Hydroxymethylpyridyl-2)-4-methyl-2-phenyl-piperazine (1.8 g) is added to ˜5 mL of concentrated sulfuric acid. The resulting solution is mixed at 350° C. for 6 hours. After cooling, the reaction mixture is added to 25 g of ice under mixing and basified with a concentrated ammonia solution or sodium hydroxide solution to pH=10. The separated precipitate is extracted into methylene chloride and the extract is evaporated to dryness; 1.6 g of Mirtazapine is obtained (yield 95%).

Workup

  1. additionThe resulting solution is mixed at 350° C. for 6 hours
  2. temperatureAfter cooling
  3. additionunder mixing
  4. extractionThe separated precipitate is extracted into methylene chloride
  5. customthe extract is evaporated to dryness

Sources & evidence

ORD record
ord-77349d81ba8442899937127503f714bc
Source dataset
uspto-grants-2003_06
Patent number
US06576764B2

Reaction notes

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