Tert-Butylamine → HCID 23135960, compound

HRID 1777005Notes

Reaction equation

HRID 1777005 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2C([NH:9][C:10](=[O:11])[C:5]=12)=O.[C:15]([NH2:19])([CH3:18])([CH3:17])[CH3:16].[C:20](=[O:23])([O-])[O-].[K+].[K+]>CN(C)C=O>[C:15]([NH:19][CH2:2][CH2:3][C:4]12[CH:14]=[CH:13][CH:12]=[CH:6][CH:5]1[C:10]([NH:9][C:20]2=[O:23])=[O:11])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 11430Potassium CarbonateHCID 219600212-Bromoethylphthalimide

Product 1

HCID 23135960HCID 23135960, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-bromoethyl phthalimide (20 g, 2 equiv), tert-butylamine (41 ml, 1 equiv) and potassium carbonate (10.86 g, 2 equiv) in dimethylformamide (200 ml) was heated to 50° C. for 48 hours. Solvent was evaporated and the residue partitioned between dichloromethane and water. The organic phase was dried (K2CO3) and solvent removed to afford the title compound as an orange solid (18.93 g). 1H-NMR (CDCl3) δ 1.05 (9H,s), 2.85 (2H,t), 3.77 (2H,t), 7.72 (2H,m), 7.85 (2H,m).

Workup

  1. customSolvent was evaporated
  2. customthe residue partitioned between dichloromethane and water
  3. dry with materialThe organic phase was dried (K2CO3) and solvent
  4. customremoved

Sources & evidence

ORD record
ord-ba0fc3dbfa1f4e34a02aacc0f63f0a1c
Source dataset
uspto-grants-2016_02
Patent number
US09266841B2

Reaction notes

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