Trifluoroacetic acid → HCID 59600612, compound

HRID 2267103Notes

Reaction equation

HRID 2267103 reaction equation
[C:1]([C:3]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:6]2([CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]2)[CH2:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>ClCCl>[NH:9]1[CH2:8][CH2:7][C:6]2([C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:3]([C:1]#[N:2])=[CH:4][CH2:5]2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68681909HCID 68681909, compound

Product 1

HCID 59600612HCID 59600612, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the nitrile (A3) (300 mg) in dichloromethane (3 ml) was treated with TFA (1 ml) for 1 hour, concentrated, co-evaporated with acetonitrile and dissolved in dichloromethane (ca. 100 ml). The resulting solution was washed with a mixture of brine (ca. 20 ml) and 6N NaOH (2 ml), dried over Na2SO4, and concentrated to give 2H-spiro[naphthalene-1,4′-piperidine]-4-carbonitrile (A4) as a white solid. LC-MS: m/e=225.2 (M+H). Rt=1.53 min.

Workup

  1. concentrationconcentrated, co-evaporated with acetonitrile
  2. dissolutiondissolved in dichloromethane (ca. 100 ml)
  3. washThe resulting solution was washed with a mixture of brine (ca. 20 ml) and 6N NaOH (2 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-28b4305c8fed412c9d6f6934733bcfb8
Source dataset
uspto-grants-2010_12
Patent number
US07858790B2

Reaction notes

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