Potassium Hydroxide → HCID 18545204, compound

HRID 1266999Notes

Reaction equation

HRID 1266999 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:14][CH:13]3[N:15]([CH2:16][CH2:17][CH2:18][NH:19]C(=O)C(F)(F)F)[CH:10]([CH2:11][CH2:12]3)[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:9][CH:10]3[N:15]([CH2:16][CH2:17][CH2:18][NH2:19])[CH:13]([CH2:12][CH2:11]3)[CH:14]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18545197HCID 18545197, compound

Product 1

HCID 18545204HCID 18545204, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Racemic N-{3-[3-(4-Chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-en-8-yl]-propyl}-2,2,2-trifluoroacetamide (0.73 g, 1.96 mmol) and 20% potassium hydroxide (2.8 mL) were combined in ethanol (12 mL) and stirred at room temperature for 24 hours. Reaction was concentrated, dissolved in methylene chloride (200 mL), added sodium sulfate and stirred for 15 hours. The mix was filtered through Celite and concentrated to yield 3-[3-(4-Chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-2-en-8-yl]-propylamine.

Workup

  1. customReaction
  2. concentrationwas concentrated
  3. dissolutiondissolved in methylene chloride (200 mL)
  4. additionadded sodium sulfate
  5. stirringstirred for 15 hours
  6. filtrationThe mix was filtered through Celite
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a5a07c990e27464c8285ec5340c69bcd
Source dataset
uspto-grants-2003_04
Patent number
US06552015B2

Reaction notes

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