N,N'-Dimethylethylenediamine → Tert-butyl benzyl[(3-{methyl[2-(methylamino)ethyl]amino}propyl)sulfonyl]carbamate

HRID 421957Notes

Reaction equation

HRID 421957 reaction equation
[CH2:1]([N:8]([S:16]([CH2:19][CH2:20][CH2:21]Cl)(=[O:18])=[O:17])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][NH:24][CH2:25][CH2:26][NH:27][CH3:28].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:1]([N:8]([S:16]([CH2:19][CH2:20][CH2:21][N:24]([CH3:23])[CH2:25][CH2:26][NH:27][CH3:28])(=[O:18])=[O:17])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 66674695Tert-butyl benzyl[(3-chloropropyl)sulfonyl]carbamate

Product 1

HCID 66674500Tert-butyl benzyl[(3-{methyl[2-(methylamino)ethyl]amino}propyl)sulfonyl]carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

Tert-butyl benzyl[(3-chloropropyl)sulfonyl]carbamate was dissolved in MeCN (0.2M) and N,N′-dimethylethane-1,2-diamine (5 eq.) was added followed by K2CO3 (5 eq.). The mixture was stirred at 65° C. overnight. The solvent was removed under reduced pressure and the residual material was dissolved in EtOAc and washed with water. After drying over Na2SO4, all volatiles were evaporated in vacuo and the residual material used in the next step without purification. (ES+) m/z 400 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residual material was dissolved in EtOAc
  3. washwashed with water
  4. dry with materialAfter drying over Na2SO4
  5. customall volatiles were evaporated in vacuo
  6. customthe residual material used in the next step without purification

Sources & evidence

ORD record
ord-6114f5e9ee34417b88de6e74431dcf1f
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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