Dimethylacetamide → HCID 178457241, compound

HRID 25536

Reaction equation

HRID 25536 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19]Br)[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:22]([CH2:25][NH2:26])[CH:23]=C.[CH3:27]C(N(C)C)=O>>[C:1]([O:5][C:6](=[O:21])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][N:26]([CH2:25][CH:22]=[CH2:23])[CH3:27])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 31374DimethylacetamideHCID 4437323-Buten-1-amineHCID 178486057HCID 178486057, compound

Product 1

HCID 178457241HCID 178457241, compoundYield 92%

Procedure

To 1.7 g (4.7 mmol) trans-[4-(4-Bromo-butoxy)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 22 ml DMA, 1.34 ml (14 mmol, 3 eq) N-allylmethylamine were added over a period of 10 min. The reaction was stirred at RT over night, concentrated and the residue was dissolved in CH2Cl2/5% aqueous NaHCO3. The phases were separated and the inorganic phase was extracted with CH2Cl2, the combined organic phases were washed with brine, dried over Na2SO4 and concentrated to yield 1.5 g (92%) trans-(4-[4-(Allyl-methyl-amino)-butoxy]-cyclohexyl)-methyl-carbamic acid tert-butyl ester as colorless oil, MS: 355 (MH+).

Workup

  1. concentrationconcentrated
  2. dissolutionthe residue was dissolved in CH2Cl2/5% aqueous NaHCO3
  3. customThe phases were separated
  4. extractionthe inorganic phase was extracted with CH2Cl2
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4128066c2cac404680c12d215436bd84
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Linked notes

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