Potassium Carbonate → benzyl N,N-bis(prop-2-yn-1-yl)carbamate

HRID 1406798Notes

Reaction equation

HRID 1406798 reaction equation
[CH2:1]([NH:4][CH2:5][C:6]#[CH:7])[C:2]#[CH:3].C([O-])([O-])=O.[K+].[K+].[CH2:14]([O:21][C:22](ON1C(=O)CCC1=O)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCOC(C)=O.[Cl-].[Na+].O>[CH2:14]([O:21][C:22](=[O:23])[N:4]([CH2:5][C:6]#[CH:7])[CH2:1][C:2]#[CH:3])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 23350DipropargylamineHCID 83172Benzyl succinimido carbonate

Product 1

HCID 14358054benzyl N,N-bis(prop-2-yn-1-yl)carbamate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent3×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of dipropargylamine (46.7 g, 502 mmol) in EtOAc (200 mL) and 10% aqueous K2CO3 (700 mL, 507 mmol) was slowly added a solution of N-(benzyloxycarbonyloxy)succinimide (125 g, 502 mmol) in EtOAc (500 mL) over 20 mins. The solution was stirred at 0° C. for 2 h then at RT 16 h. The phases were separated and the organic phase was washed with 10% aqueous K2CO3 (700 mL, 507 mmol) and then with saturated brine (500 mL) and was diluted to 1000 mL with EtOAc to give a 0.5M solution.

Workup

  1. customat RT
  2. custom16 h
  3. customThe phases were separated

Sources & evidence

ORD record
ord-af990712596e4b5483cc28b2f8e3ac63
Source dataset
uspto-grants-2014_12
Patent number
US08916552B2

Reaction notes

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