1,4-Dioxane → 3-{2-[4-(2,6-Dichloro-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid hydrochloride

HRID 920595Notes

Reaction equation

HRID 920595 reaction equation
C([O:5][C:6](=[O:31])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:30])=[CH:17][CH:16]=2)[CH2:10]1)(C)(C)C.O1CCOCC1>Cl>[ClH:29].[Cl:29][C:28]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:30])[C:23]=1[CH2:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([CH:11]2[O:12][CH2:13][CH2:14][N:9]([CH2:8][CH2:7][C:6]([OH:31])=[O:5])[CH2:10]2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 670325163-{2-[4-(2,6-Dichloro-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid tert-butyl ester

Product 1

HCID 670325523-{2-[4-(2,6-Dichloro-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid hydrochlorideYield 176.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-{2-[4-(2,6-Dichloro-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid tert-butyl ester (0.59 g; 1.27 mmol) was dissolved in a 4M solution of HCl in 1,4-dioxane (6.33 mL, 25.30 mmol) and stirred overnight at RT. Subsequently, the solvent was removed in vacuo and the residue treated with iPr2O, the precipitate was collected by filtration and dried overnight under reduced pressure to afford 3-{2-[4-(2,6-Dichloro-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid hydrochloride (0.50 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.88-2.97 (2 H, m) 3.11 (1 H, t, J=11.7 Hz) 3.15-3.23 (1 H, m) 3.30-3.43 (2 H, m) 3.49 (1 H, d, J=12.0 Hz) 3.55-3.64 (1 H, m) 4.01-4.20 (2 H, m) 4.88 (1 H, d, J=12.0 Hz) 5.24 (2 H, s) 7.04-7.12 (2 H, m) 7.35 (2 H, d, J=8.7 Hz) 7.40-7.49 (1 H, m) 7.49-7.56 (2 H, m).

Workup

  1. customSubsequently, the solvent was removed in vacuo
  2. additionthe residue treated with iPr2O
  3. filtrationthe precipitate was collected by filtration
  4. customdried overnight under reduced pressure

Sources & evidence

ORD record
ord-88260d38174f45119be8f44da749232c
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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