Diisopropylethylamine → benzyl N-methyl-N-[(3-nitrophenyl)methyl]carbamate

HRID 735652Notes

Reaction equation

HRID 735652 reaction equation
[C:1](=[O:18])(ON1C(=O)CCC1=O)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:19][NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:19][N:20]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=1)[C:1](=[O:18])[O:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83172Benzyl succinimido carbonateHCID 409439N-methyl-1-(3-nitrophenyl)methanamine

Product 1

HCID 57842906benzyl N-methyl-N-[(3-nitrophenyl)methyl]carbamateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzyl 2,5-dioxopyrrolidin-1-yl carbonate (1.65 g, 6.6 mmol) was added to a solution of N-methyl-1-(3-nitrophenyl)methanamine (1 g, 6 mmol) in CH2Cl2 (24 mL) and DIEA (2.7 mL, 15 mmol) and the reaction mixture was stirred for 1 h. The mixture was diluted with CH2Cl2 (100 mL), washed with NH4Cl, NaHCO3, brine, dried over Na2SO4 and concentrated in vacuo to yield 60A (1.75 g, 99%) as a white solid. MS (ESI) m/z 301.03 (M+H)+.

Workup

  1. washwashed with NH4Cl, NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a1af5fa02b343e9ba6ef7f00bbeb47c
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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