N,N-Dimethylglycine → Phenylmethyl 4-[2-(dimethylamino)acetyl]-1-piperazinecarboxylate

HRID 2376851Notes

Reaction equation

HRID 2376851 reaction equation
N1([NH:7][C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])CCNCC1.[CH3:18][N:19]([CH3:24])[CH2:20][C:21](O)=[O:22].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[CH2:48]([N:50](CC)[CH2:51][CH3:52])[CH3:49]>O1CCCC1>[CH3:18][N:19]([CH3:24])[CH2:20][C:21]([N:50]1[CH2:51][CH2:52][N:7]([C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:9])[CH2:49][CH2:48]1)=[O:22]

Participants

7

Reactant 5

HCID 673N,N-DimethylglycineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69316859HCID 69316859, compound

Product 1

HCID 21054865Phenylmethyl 4-[2-(dimethylamino)acetyl]-1-piperazinecarboxylateYield 31.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl piperazine-1-carbamate (2.203 g, 10.0 mmol) was dissolved in tetrahydrofuran (50 ml); 2-dimethylaminoacetic acid (1.24 g, 12.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.30 g, 12.0 mmol), 1-hydroxy-1H-benzotriazole monohydrate (1.84 g, 12.0 mmol) and triethylamine (3.35 ml, 24.0 mmol) were added thereto; and the reaction mixture was stirred at room temperature for 7 hours. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and brine, dried over anhydrous sodium sulfate, and the residue was purified by NH silica gel column chromatography (eluent; ethyl acetate:hexane=3:1) to yield the title compound (954 mg, 3.12 mmol, 31.2%) as a colorless oil.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe residue was purified by NH silica gel column chromatography (eluent; ethyl acetate:hexane=3:1)

Sources & evidence

ORD record
ord-914c80ad19f1403a927d8fa87cf6e050
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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