Methylamine → HCID 68413945, compound

HRID 220254Notes

Reaction equation

HRID 220254 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:13][CH2:14][C:15]([OH:17])=O)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].C[CH2:19][N:20](C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CN>C1COCC1.C(Cl)CCl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:13][CH2:14][C:15]([NH:20][CH3:19])=[O:17])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

7

Reactant 4

HCID 6329Methylamine2×HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 3161664HCID 3161664, compound

Product 1

HCID 68413945HCID 68413945, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 0.72 g of 3-(3,4-diethoxy-phenyl)-propionic acid in 10 mL THF were added 1.6 mL of DIPEA, 0.45 g of HOBt, 0.63 g of EDC and 10 mL of MeNH2 (2M in THF). The reaction mixture was heated in a closed vessel overnight at 70° C. Further additions of MeNH2 were done during the next 12 h. The mixture was then concentrated in vacuo, the residue was taken up in sat. aq. NaHCO3 and washed with EtOAc (2×). The organic layers were combined, washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by CC with EtOAc yielded 0.16 g of 3-(3,4-diethoxy-phenyl)-N-methyl-propionamide as solid.

Workup

  1. customwere done during the next 12 h
  2. concentrationThe mixture was then concentrated in vacuo
  3. washwashed with EtOAc (2×)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by CC with EtOAc

Sources & evidence

ORD record
ord-46f76b843a4a402dbb9b0592528d1678
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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