Hydrochloric Acid → Morpholine-2-carboxylic acid hydrochloride

HRID 1435519Notes

Reaction equation

HRID 1435519 reaction equation
CC(OC([N:8]1[CH2:13][CH:12]([C:14]([OH:16])=[O:15])[O:11][CH2:10][CH2:9]1)=O)(C)C.[ClH:17]>O1CCOCC1>[ClH:17].[NH:8]1[CH2:9][CH2:10][O:11][CH:12]([C:14]([OH:16])=[O:15])[CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acid

Product 1

HCID 42614320Morpholine-2-carboxylic acid hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(R,S)-Boc-2-carboxymorpholine (3 g, 13 mmol) was added to 4 N HCl in dioxane (15 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. Removal of solvent produced 2.2 g (100%) of the desired product as an HCl salt. 1H NMR (400 MHz, METHANOL-D4) δ 2.79-2.86 (m, 1 H), 2.87-2.94 (m, 2 H), 3.21 (dd, J=12.50, 3.52 Hz, 1 H), 3.51 (m, 1 H), 3.79 (m, 1 H), 4.07 (dd, J=9.77, 3.12 Hz, 1 H).

Workup

  1. customRemoval of solvent

Sources & evidence

ORD record
ord-1f523e8acc8941e9947d7d41ab501449
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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