Diethyl Ether → Aminoethanol diclofenac Hydrochloride

HRID 1360002Notes

Reaction equation

HRID 1360002 reaction equation
[C:1]([C:8]([NH2:11])([OH:10])C)(OC(C)(C)C)=O.[CH:12]1[CH:13]=[CH:14][C:15]([NH:22][C:23]2[C:24]([Cl:30])=[CH:25][CH:26]=[CH:27][C:28]=2[Cl:29])=[C:16]([CH2:18][C:19]([OH:21])=[O:20])[CH:17]=1.[ClH:31].C(OCC)(=O)C.C(OCC)C.CCCCCC>ClCCl>[NH2:11][CH:8]([OH:10])[CH3:1].[CH:12]1[CH:13]=[CH:14][C:15]([NH:22][C:23]2[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:30])=[C:16]([CH2:18][C:19]([OH:21])=[O:20])[CH:17]=1.[ClH:31]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 21866389Hydrogen chloride-ethyl acetateHCID 86623053Boc-aminoethanol diclofenac

Product 1

HCID 86623054Aminoethanol diclofenac HydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 5 ml of dichloromethane, 2.108 g (4.80 mmol) of the Boc-aminoethanol-diclofenac obtained above was dissolved, and 20 ml of 4 M hydrochloric acid/ethyl acetate was added thereto under ice-cooling, followed by stirring for 2.5 hours. Diethyl ether and hexane were added thereto for precipitation, and the precipitate was dried under reduced pressure to give 1.775 g (98%) of the titled compound. The structure was identified by 1H-NMR.

Workup

  1. dissolutionabove was dissolved
  2. temperatureunder ice-cooling
  3. customfor precipitation
  4. customthe precipitate was dried under reduced pressure

Sources & evidence

ORD record
ord-ceefd64c0cea4f2883ba1495c06c4f51
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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