N-{4-[3-(4-Chloro-phenyl)-3,8-diaza-bicyclo[3.2.1]oct-8-yl]-butyl}-2,2,2-trifluoro-acetamide → 4-[3-(4-Chloro-phenyl)-3,8-diaza-bicyclo[3.2.1]oct-8-yl]-butylamine

HRID 1266986Notes

Reaction equation

HRID 1266986 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH:13]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20]C(=O)C(F)(F)F)[CH:10]([CH2:11][CH2:12]3)[CH2:9]2)=[CH:4][CH:3]=1>C(O)C.[OH-].[K+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][CH:13]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH:10]([CH2:11][CH2:12]3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 18545195N-{4-[3-(4-Chloro-phenyl)-3,8-diaza-bicyclo[3.2.1]oct-8-yl]-butyl}-2,2,2-trifluoro-acetamide

Product 1

HCID 185451914-[3-(4-Chloro-phenyl)-3,8-diaza-bicyclo[3.2.1]oct-8-yl]-butylamineYield 94.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

N-{4-[3-(4-Chloro-phenyl)-3,8-diaza-bicyclo[3.2.1]oct-8-yl]-butyl}-2,2,2-trifluoro-acetamide (0.88 g, 2.26 mmol) was dissolved in ethanol (18 mL) and 20% potassium hydroxide (3.26 mL). The clear solution was stirred for 3 hours, concentrated to dryness, diluted with methylene chloride (500 mL), added sodium sulfate and stirred for 3 hours. The mixture was filtered through Celite and concentrated to yield 4-[3-(4-Chloro-phenyl)-3,8-diaza-bicyclo[3.2.1]oct-8-yl]-butylamin (0.63 g, 94.9%) as a golden oil which had the following properties: 1H NMR CDCl3 δ: 7.14 (d, J=9.1 Hz, 2H), 6.68 (d, J=9.1 Hz, 2H), 3.35 (brd s, 2H), 3.26 (d, J=13.7 Hz, 2H), 2.96 (d, J=9.1 Hz, 2H), 2.75-2.68 (m, 2H), 2.47-2.18 (m, 4H), 1.98-1.88 (m, 2H), 1.76-1.67 (m, 2H), 1.69-1.45 (m, 4H).

Workup

  1. concentrationconcentrated to dryness
  2. additiondiluted with methylene chloride (500 mL)
  3. additionadded sodium sulfate
  4. stirringstirred for 3 hours
  5. filtrationThe mixture was filtered through Celite
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1efeba73f8404106b56bfd7cde8eba06
Source dataset
uspto-grants-2003_04
Patent number
US06552015B2

Reaction notes

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