Trifluoroacetic acid → HCID 86698022, compound

HRID 518869Notes

Reaction equation

HRID 518869 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][CH2:20][C@@H:19]([NH:23]C(=O)OC(C)(C)C)[CH2:18]2)=[CH:13][C:12]=1[O:31][CH:32]([CH3:34])[CH3:33])([O-:10])=[O:9]>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][CH2:20][C@@H:19]([NH2:23])[CH2:18]2)=[CH:13][C:12]=1[O:31][CH:32]([CH3:34])[CH3:33])([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 86698024HCID 86698024, compound

Product 1

HCID 86698022HCID 86698022, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.25 ml of trifluoroacetic acid are added, at a temperature of about 20° C., to 5.32 g of 2-methylpropan-2-yl {(3R)-1-[4-nitro-3-(propan-2-yloxy)phenyl]piperidin-3-yl}carbamate in solution in 106 ml of dichloromethane, and the mixture is left to stir for 15 h. A further 2 ml of trifluoroacetic acid are added and the stirring is continued for 1 h. The mixture is concentrated under reduced pressure, so as to obtain an oily residue which is precipitated by adding ethyl ether. The solid obtained is filtered off and then washed with ethyl ether, so as to obtain 5.42 g of (3R)-1-[4-nitro-3-(propan-2-yloxy)phenyl]piperidin-3-amine trifluoroacetate in the form of a yellow solid.

Workup

  1. waitthe mixture is left
  2. waitthe stirring is continued for 1 h
  3. concentrationThe mixture is concentrated under reduced pressure
  4. customso as to obtain an oily residue which
  5. customis precipitated
  6. additionby adding ethyl ether
  7. customThe solid obtained
  8. filtrationis filtered off
  9. washwashed with ethyl ether

Sources & evidence

ORD record
ord-7525e3a9fbae4830a240d7a1bc19731c
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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