Trifluoroacetic acid → HCID 68576434, compound

HRID 272945Notes

Reaction equation

HRID 272945 reaction equation
[C:1]([C:3]1([C:9]2[CH:28]=[CH:27][C:12]([O:13][CH:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)=[CH:11][CH:10]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].C(O)(C(F)(F)F)=O>ClCCl>[NH:17]1[CH2:16][CH2:15][CH:14]([O:13][C:12]2[CH:11]=[CH:10][C:9]([C:3]3([C:1]#[N:2])[CH2:4][CH2:5][O:6][CH2:7][CH2:8]3)=[CH:28][CH:27]=2)[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23091694HCID 23091694, compound

Product 1

HCID 68576434HCID 68576434, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-[4-(4-cyanotetrahydro-2H-pyran-4-yl)phenoxy]-1-piperidinecarboxylate (720 mg) was dissolved in dichloromethane (50 ml) at 0° C. TFA (10 ml) was added and the mixture stirred whilst warming to room temperature over 2 hours. The reaction mixture was then concentrated in vacuo, and partitioned between dichloromethane (80 ml) and 0.5M NaOH (50 ml). The dichlorormethane solution was dried over Na2SO4 and evaporated to give 4-[4-(4-piperidinyloxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile as a colorless oil which crystallized on standing (500 mg, 94%).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. custompartitioned between dichloromethane (80 ml) and 0.5M NaOH (50 ml)
  3. dry with materialThe dichlorormethane solution was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-5262357ae1134274af00048bb15d338b
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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