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

HRID 2167914Notes

Reaction equation

HRID 2167914 reaction equation
[Cl:1]C1C=CC=C(Cl)C=1COC1C=CC(C2OCCN(CCC(O)=O)C2)=CC=1.C([O:32][C:33](=[O:58])[CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][O:39][CH:38]([C:42]2[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]3[C:55]([Cl:56])=[CH:54][CH:53]=[CH:52][C:51]=3[Cl:57])=[CH:44][CH:43]=2)[CH2:37]1)(C)(C)C.O1CCOCC1>Cl>[ClH:1].[Cl:56][C:55]1[CH:54]=[CH:53][CH:52]=[C:51]([Cl:57])[C:50]=1[CH2:49][O:48][C:45]1[CH:44]=[CH:43][C:42]([CH:38]2[O:39][CH2:40][CH2:41][N:36]([CH2:35][CH2:34][C:33]([OH:58])=[O:32])[CH2:37]2)=[CH:47][CH:46]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 670325163-{2-[4-(2,6-Dichloro-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid tert-butyl esterHCID 670325533-{2-[4-(2,6-Dichloro-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3-{2-[4-(2,6-Dichloro-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid. 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 (2H, m) 3.11 (1H, t, J=11.7 Hz) 3.15-3.23 (1H, m) 3.30-3.43 (2H, m) 3.49 (1H, d, J=12.0 Hz) 3.55-3.64 (1H, m) 4.01-4.20 (2H, m) 4.88 (1H, d, J=12.0 Hz) 5.24 (2H, s) 7.04-7.12 (2H, m) 7.35 (2H, d, J=8.7 Hz) 7.40-7.49 (1H, m) 7.49-7.56 (2H, 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-be555cf6d1db4d21956eb41ca4b224ab
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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