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Trifluoroacetic acid → N-(3-hydroxy-3-methylbutyl)-N-{[2,4-dichlorophenyl]-methyl}-azetidine-3-yl-methylamine

HRID 1435156
Notes
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Reaction equation

HRID 1435156 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([CH2:12][N:13]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[CH2:14][CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[CH2:9]1)=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[OH:19][C:16]([CH3:18])([CH3:17])[CH2:15][CH2:14][N:13]([CH2:12][CH:10]1[CH2:11][NH:8][CH2:9]1)[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[Cl:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 690038323-{[(2,4-Dichlorobenzyl)-(3-hydroxy-3-methyl-butyl)-amino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 57937779N-(3-hydroxy-3-methylbutyl)-N-{[2,4-dichlorophenyl]-methyl}-azetidine-3-yl-methylamineYield 87%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

3-{[(2,4-dichlorobenzyl)-(3-hydroxy-3-methyl-butyl)-amino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester (88 mg, 0.2 mmol) is added to a stirred solution of dichloromethane (1.0 mL) and anisole (1.5 mL). Trifluoroacetic acid (0.6 mL) is added and the reaction is stirred for 2 h at room temperature. The reaction is concentrated to half volume and loaded onto a SCX-2 (10 g) column and washed with methanol (40 mL). The product is then eluted with 2M ammonia in methanol (25 mL) and concentrated to yield (57 mg, 87%) of N-(3-hydroxy-3-methylbutyl)-N-{[2,4-dichlorophenyl]-methyl}-azetidine-3-yl-methylamine. 1H NMR (400 MHz, CD3OD) δH: 7.49-7.47 (2H, m), 7.36-7.33 (1H, m), 3.80-3.70 (2H, m), 3.65 (2H, s), 3.49-3.40 (2H, m), 3.16-3.06 (1H, m), 2.79-2.77 (2H, m), 2.67 (2H, t, J=7.3 Hz), 1.69 (2H, t, J=7.3 Hz), 1.1 (6H, s). Mass spectrum (ion spray): m/z=331.2 (M+H).

Workup

  1. concentrationThe reaction is concentrated to half volume
  2. washwashed with methanol (40 mL)
  3. washThe product is then eluted with 2M ammonia in methanol (25 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8511230dbb68459b98958679eb472281
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07615648B2

Reaction notes

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