Hydrochloric Acid → N-(4-{2-[4-(aminomethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide

HRID 2117866Notes

Reaction equation

HRID 2117866 reaction equation
C([N:3]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[N:16]=[C:17]([NH:20][C:21](=[O:23])[CH3:22])[S:18][CH:19]=2)=[CH:9][CH:8]=1)C=O)=O.Cl>CO.C(OCC)(=O)C>[NH2:3][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[N:16]=[C:17]([NH:20][C:21](=[O:23])[CH3:22])[S:18][CH:19]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21914877HCID 21914877, compound

Product 1

HCID 21915165N-(4-{2-[4-(aminomethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamideYield 107.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-[4-(2-{4-[(diformylamino)methyl]-phenyl}ethyl)-1,3-thiazol-2-yl]acetamide (56 mg) in methanol (0.5 ml) was added 4N hydrogen chloride in ethyl acetate (0.5 ml), and the mixture was stirred at ambient temperature for 1 hour. The reaction mixture was concentrated in vacuo. The residue was separated between chloroform (5 ml) and saturated aqueous sodium hydrogen bicarbonate (5 ml), and the aqueous layer was extracted with chloroform (5 ml). The organic layer was dried over sodium sulfate and concentrated in vacuo to give N-(4-{2-[4-(aminomethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (50 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was separated between chloroform (5 ml) and saturated aqueous sodium hydrogen bicarbonate (5 ml)
  3. extractionthe aqueous layer was extracted with chloroform (5 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49a615527c4c40b0b8836ef0782a428e
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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