Hydrochloric Acid → Fadrozole

HRID 22569Notes

Reaction equation

HRID 22569 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][CH2:12][C:13]2[N:14]=[CH:15][NH:16][CH:17]=2)=[CH:5][CH:4]=1)#[N:2].C([BH3-])#N.[Na+].Cl>CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[CH:15]=[N:16][CH:17]=[C:13]3[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 178509866HCID 178509866, compound

Product 1

HCID 59693Fadrozole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.24 g of 1-(p-cyanophenyl)-4-(4-imidazolyl)-1-butanone in 20 ml of methanol at room temperature is treated with 0.2 g of sodium cyanoborohydride. The pH is adjusted and maintained at 5.5-6.0 by addition of concentrated hydrochloric acid. The reaction mixture is stirred for 2 h, adjusted to pH 2, and evaporated to dryness. The residue is taken up in methylene chloride and washed with saturated sodium bicarbonate. The organic layer is dried over sodium sulfate and evaporated to yield 5-(p-cyanophenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine.

Workup

  1. customevaporated to dryness
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-1b02ea0a2fb74ae6bd326205943624fa
Source dataset
uspto-grants-1995_06
Patent number
US05428160

Reaction notes

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