Trifluoroacetic acid → HCID 59600645, compound

HRID 2267107Notes

Reaction equation

HRID 2267107 reaction equation
[CH3:1][N:2]([CH3:27])[C:3]([C:5]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:8]2([CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH2:7][CH:6]=1)=[O:4].C(O)(C(F)(F)F)=O>ClCCl>[CH3:1][N:2]([CH3:27])[C:3]([C:5]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:8]2([CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59600651HCID 59600651, compound

Product 1

HCID 59600645HCID 59600645, compoundYield 118.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the dimethylamide (B2) (156 mg) in dichloromethane (5 ml) was treated with TFA (1 ml) for 1 h. After concentration and co-evaporation with acetonitrile, the residue was dissolved in dichloromethane, washed with a mixture of brine and 1 ml 6N NaOH, dried (Na2SO4), and concentrated to give N,N-dimethyl-2H-spiro[naphthalene-1,4′-piperidine]-4-carboxamide (B3) (135 mg). LC-MS: m/e=271.0 (M+H). Rt=1.30 min.

Workup

  1. concentrationAfter concentration and co-evaporation with acetonitrile
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with a mixture of brine and 1 ml 6N NaOH
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-89920ab23a51455e981ad506353ef57a
Source dataset
uspto-grants-2010_12
Patent number
US07858790B2

Reaction notes

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