Diisopropylethylamine → tert-Butyl dibenzylcarbamate

HRID 1174506Notes

Reaction equation

HRID 1174506 reaction equation
COC([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)=O.[CH:19](N(C(C)C)CC)(C)C.[O:28](C(OC(C)(C)C)=O)[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=O>C(Cl)Cl>[C:29]([N:11]([CH2:8][C:7]1[CH:6]=[CH:5][CH:10]=[CH:9][CH:19]=1)[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:28]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 14425149Methyl 4-(benzylamino)benzoate

Product 1

HCID 15395220tert-Butyl dibenzylcarbamateYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-(4-methoxycarbonylphenyl)benylamine (25 g, 0.098 mol) in CH2Cl2 (500 ml), was added diisopropyl ethylamine (38 g, 0.294 mol) and (BOC)2O (32 g, 0.147 mol). After stirring at r.t. for 5 h, the solvent was removed under reduce pressure. The crude product was then purified by chromatography using chloroform/methanol (9/1) to afford 4-methoxy carbonyl-[N-(BOC]-N-[benzyl]benzylamine (27 g, 78%) as a liquid.

Workup

  1. customthe solvent was removed
  2. customThe crude product was then purified by chromatography

Sources & evidence

ORD record
ord-702b44976e1347a4bd32e1ca3c283da8
Source dataset
uspto-grants-2010_11
Patent number
US07838522B2

Reaction notes

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