Dimethylamine, hydrochloride → HCID 15117492, compound

HRID 2262152Notes

Reaction equation

HRID 2262152 reaction equation
C(NCC(O)=O)(OC[C:5]1[CH:10]=[CH:9]C=[CH:7][CH:6]=1)=O.C([N:19]([CH:22]([CH3:24])C)[CH2:20][CH3:21])(C)C.C[CH2:26][N:27]=[C:28]=NCCCN(C)C.Cl.C1C=NC2N([OH:46])N=NC=2C=1.Cl.CNC>CN(C=O)C.C(OCC)(=O)C>[CH2:22]([NH:19][CH2:20][C:21]([N:27]([CH3:28])[CH3:26])=[O:46])[C:24]1[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 14349BenzyloxycarbonylglycineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 15117492HCID 15117492, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Cbz Glycine (9.6 mmol) was dissolved in DMF (30 mL). Diisopropylethylamine (40 mmol), EDC HCl (10 mmol), HOAt (10 mmol) and dimethylamine hydrochloride (10 mmol) were subsequently added to the solution. The reaction was allowed to stir overnight. Ethyl acetate (100 mL) was added to the solution and the organic was washed with 1 N HCl followed by a wash with an aqueous solution of saturated sodium bicarbonate. The organic layer was dried with magnesium sulfate and concentrated to give 1.02 g of 2-(benzylamino)-N,N-dimethylacetamide. 2-(benzylamino)-N,N-dimethylacetamide (4.3 mmol) was dissolved in methanol (20 mL) and combined with 5% loaded Pd/C (0.21 mmol). The solution was stirred under a hydrogen filled balloon for four hours then filtered through celite and concentrated to give 402 mg of 2-amino-N,N-dimethylacetamide as a yellow oil.

Workup

  1. washthe organic was washed with 1 N HCl
  2. washa wash with an aqueous solution of saturated sodium bicarbonate
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-db054a8511ab4fc6bac91f219d976169
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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