Trifluoroacetic acid → 5-(methyloxy)-1-(piperazin-1-ylmethyl)-3,4-dihydro-1H-isochromene-6-carbonitrile

HRID 2173288Notes

Reaction equation

HRID 2173288 reaction equation
[C:1]([C:3]1[C:4]([O:27][CH3:28])=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH2:13][N:14]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]1)[O:8][CH2:7][CH2:6]2)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:28][O:27][C:4]1[C:3]([C:1]#[N:2])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][O:8][CH:9]2[CH2:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67517697tert-butyl 4-[(6-cyano-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate

Product 1

HCID 675156135-(methyloxy)-1-(piperazin-1-ylmethyl)-3,4-dihydro-1H-isochromene-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[(6-cyano-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate (30 mg, 0.08 mmol) in 5 mL of DCM was added 5 mL of TFA was stirred at room temperature for 1 hours, and the reaction was concentrated to afford 5-methoxy-1-(piperazin-1-ylmethyl)-3,4-dihydro-1H-isochromene-6-carbonitrile.

Workup

  1. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-6ac0081a90c442ff96e0cf7ec4479567
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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