L-Tartaric acid → N-(3-Hydroxy-3-methylbutyl)-N-{[2,4-dichlorophenyl]-methyl}-azetidine-3-yl-methylamine L-Tartrate

HRID 1435157Notes

Reaction equation

HRID 1435157 reaction equation
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[OH:11][C:12]([CH3:31])([CH3:30])[CH2:13][CH2:14][N:15]([CH2:25][CH:26]1[CH2:29][NH:28][CH2:27]1)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24]>CO>[C:6]([C@@H:4]([C@H:2]([C:1]([OH:10])=[O:9])[OH:3])[OH:5])([OH:8])=[O:7].[OH:11][C:12]([CH3:31])([CH3:30])[CH2:13][CH2:14][N:15]([CH2:25][CH:26]1[CH2:29][NH:28][CH2:27]1)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24]

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 57937779N-(3-hydroxy-3-methylbutyl)-N-{[2,4-dichlorophenyl]-methyl}-azetidine-3-yl-methylamine

Product 1

HCID 86617386N-(3-Hydroxy-3-methylbutyl)-N-{[2,4-dichlorophenyl]-methyl}-azetidine-3-yl-methylamine L-TartrateYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

L-Tartaric acid (31.2 mg, 0.208 mmol) is added to a solution of N-(3-hydroxy-3-methylbutyl)-N-{[2,4-dichlorophenyl]-methyl}-azetidine-3-yl-methylamine (69 mg, 0.208 mmol) in methanol (2 mL). The solution is stirred for 1.5 h at ambient temperature and concentrated. The solid is dried in a vacuum oven at 45° C. overnight to yield (92 mg, 92%) of the title product. 1H NMR (400 MHz, CD3OD) δH: 7.50-7.48 (2H, m), 7.37-7.35 (1H, m), 4.5 (2H, s), 4.13-4.08 (2H, m), 3.81-3.76 (2H, m), 3.69 (2H, s), 3.25-3.20 (1H, m), 2.84-2.82 (2H, m), 2.67 (2H, t, J=7.5 Hz), 1.70 (2H, t, J=7.3 Hz), 1.1 (6H, s). Mass spectrum (ion spray): m/z=331.2 (M+H). LCMS: Rt=0.61 (3 min method).

Workup

  1. concentrationconcentrated
  2. customThe solid is dried in a vacuum oven at 45° C. overnight

Sources & evidence

ORD record
ord-37c0d6c98e2144c985461fce45a91975
Source dataset
uspto-grants-2009_11
Patent number
US07615648B2

Reaction notes

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