Tert-Butylamine → HCID 23135960, compound

HRID 859948Notes

Reaction equation

HRID 859948 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 (21H, 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-535f4b129a754b6a8bee6c98b9364559
Source dataset
uspto-grants-2006_12
Patent number
US07153861B2

Reaction notes

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