Dimethylamine → [4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-carbamic acid tert-butyl ester

HRID 1841607Notes

Reaction equation

HRID 1841607 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:25])[C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][CH2:19]OS(C)(=O)=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][NH:27][CH3:28]>CC(N(C)C)=O>[C:1]([O:5][C:6](=[O:7])[N:8]([C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][N:27]([CH3:28])[CH3:26])=[CH:11][CH:10]=1)[CH3:25])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 674Dimethylamine2×HCID 86584776Methanesulfonic acid 5-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-pent-4-ynyl ester

Product 1

HCID 68614538[4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-carbamic acid tert-butyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 1.84 g (5 mmol) of Methanesulfonic acid 5-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-pent-4-ynyl ester in 20 ml DMA was treated with 8.93 ml (50 mmol) of (33% in ethanol, 5.6 M) dimethylamine and stirred at RT for 18 h. The reaction was treated again with 4.46 ml (2 mmol) (25 mmol) of (33% in ethanol, 5.6 M) dimethylamine and stirred at RT for further 6 h. The solution was concentrated and the residual oil was extracted with aqueous sat. NaHCO3/Et2O (3×). The organic phases were washed with aqueous 10% NaCl solution, dried (Na2SO4) and evaporated to yield 1.50 g (95%) of [4-(5-Dimethylamino-pent-1-ynyl)-phenyl]-methyl-carbamic acid tert-butyl ester, MS: 317 (MH+).

Workup

  1. stirringstirred at RT for further 6 h
  2. concentrationThe solution was concentrated
  3. extractionthe residual oil was extracted with aqueous sat. NaHCO3/Et2O (3×)
  4. washThe organic phases were washed with aqueous 10% NaCl solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-af87ef457ce148a6b4926985804b8b42
Source dataset
uspto-grants-2004_01
Patent number
US06683201B2

Reaction notes

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