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Trifluoroacetic acid → N-(6-methyl-2-pyridinyl)-8-azaspiro[4.5]decane-7-methanamine

HRID 536595
Notes
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Reaction equation

HRID 536595 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH:10]2[N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17][C:12]3([CH2:16][CH2:15][CH2:14][CH2:13]3)[CH2:11]2)[CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:13]1[C:12]2([CH2:17][CH2:18][NH:19][CH:10]([CH2:9][NH:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)[CH2:11]2)[CH2:16][CH2:15][CH2:14]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66848215(+/-)Tert-butyl 7-(((6-methylpyridin-2-yl)amino)methyl)-8-azaspiro[4.5]decane-8-carboxylate2×

Product 1

HCID 67497134N-(6-methyl-2-pyridinyl)-8-azaspiro[4.5]decane-7-methanamineYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(±)tert-butyl 7-(((6-methylpyridin-2-yl)amino)methyl)-8-azaspiro[4.5]decane-8-carboxylate (intermediate 73, 1.3 g, 3.62 mmol) was dissolved in dichloromethane (10 ml) and cooled to 0° C., then trifluoroacetic acid (30 ml) was added. After 1 hour at 0° C. and 2 hours at room temperature the solution was evaporated, the residue re-dissolved in dichloromethane was washed with saturated NaHCO3 aqueous solution. The organic layers were dried (Na2SO4) and concentrated under vacuum to obtain 900 mg of the title compound.

Workup

  1. custom2 hours at room temperature the solution was evaporated
  2. dissolutionthe residue re-dissolved in dichloromethane
  3. washwas washed with saturated NaHCO3 aqueous solution
  4. dry with materialThe organic layers were dried (Na2SO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4bec20d37dd04371a148673dc83774ca
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859608B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes