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Trifluoroacetic acid → 2-Methyl-2-(piperazin-1-yl)propan-1-ol

HRID 1922713
Notes
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Reaction equation

HRID 1922713 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([CH3:18])([CH3:17])[CH2:15][OH:16])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:18][C:14]([N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)([CH3:17])[CH2:15][OH:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57420345Tert-butyl 4-(1-hydroxy-2-methylpropan-2-yl)piperazine-1-carboxylate

Product 1

HCID 120525542-Methyl-2-(piperazin-1-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-hydroxy-1,1-dimethylethyl)piperazine-1-carboxylic acid tert-butyl ester (110 mg, 0.43 mmol) in DCM (3 mL) was added TFA (1 mL) and the resulting mixture stirred for 3 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH/DCM and the product eluted with 2M NH3/MeOH affording the title compound as an off-white solid (62 mg, 91%). 1H NMR (CDCl3, 400 MHz): δ 3.32 (2H, s), 2.90 (5H, t, J=4.78 Hz), 2.38-2.13 (4H, m), 1.03 (6H, s)

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

Workup

  1. washwas washed with MeOH/DCM
  2. washthe product eluted with 2M NH3/MeOH affording the title compound as an off-white solid (62 mg, 91%)

Sources & evidence

ORD record
ord-a19c98a7912f436eaf6eeb76b7c2ef08
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08173650B2

Reaction notes

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