2-(Dimethylamino)ethanol → HCID 59737376, compound

HRID 1907730Notes

Reaction equation

HRID 1907730 reaction equation
C1N=CN([C:6]([N:8]2C=N[CH:10]=[CH:9]2)=[O:7])C=1.[CH3:13][N:14]([CH2:16][CH2:17][OH:18])[CH3:15].Cl.NCC1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1>N1C=CC=CC=1.C(Cl)Cl>[CH3:13][N:14]([CH3:15])[CH2:16][CH2:17][O:18][C:6]([NH:8][CH2:9][C:10]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)=[O:7]

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 682631,1'-CarbonyldiimidazoleHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochloride

Product 1

HCID 59737376HCID 59737376, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of carbonyl diimadzole (CDI) (609 mg, 3.76 mmol) in pyridine (5 mL) was treated with neat dimethylaminoethanol (400 μL, 3.98 mmol) and the mixture was stirred for 15 h at room temperature. Methyl 4-(aminomethyl)benzoate hydrochloride (217) (794 mg, 3.82 mmol) was then added and the reaction mixture was stirred for further 7 h, diluted with DCM, washed with saturated NaHCO3, dried over MgSO4, filtered and concentrated to produce title compound 218 as a white solid (1.16 g, >100% yield, crude, used without additional purification).

Workup

  1. stirringthe reaction mixture was stirred for further 7 h
  2. washwashed with saturated NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0d5a894d0ed94844914ebf9b6cad1b7e
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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