Dimethylformamide → 6-[5-(Allyl-methyl-amino)-pentyl]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 2212525Notes

Reaction equation

HRID 2212525 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]OS(C)(=O)=O)=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:28]([CH2:31][NH2:32])[CH:29]=C.[CH3:33]N(C=O)C>>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:32]([CH2:31][CH:28]=[CH2:29])[CH3:33])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 4437323-Buten-1-amineHCID 86587010HCID 86587010, compound

Product 1

HCID 695146476-[5-(Allyl-methyl-amino)-pentyl]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl esterYield 89%

Conditions

Temperature
70 °C

Procedure

To 560 mg (1.4 mmol) 6-(5-Methanesulfonyloxy-pentyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester in 5 ml DMF were added 2.5 ml (26.0 mmol) N-allylmethylamine. The solution was stirred at 70° C. for 2 h, concentrated and dissolved in water and CH2Cl2. 2M NaOH was added and the inorganic phase was extracted with CH2Cl2. The organic phase was washed with water and dried over Na2SO4. Purification by column chromatography with CH2Cl2/MeOH 20:1 yielded 470 mg (89%) 6-[5-(Allyl-methyl-amino)-pentyl]-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester as yellow oil, MS: 373 (MH+).

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in water
  3. addition2M NaOH was added
  4. extractionthe inorganic phase was extracted with CH2Cl2
  5. washThe organic phase was washed with water
  6. dry with materialdried over Na2SO4
  7. customPurification by column chromatography with CH2Cl2/MeOH 20:1

Sources & evidence

ORD record
ord-05050604e4cd4e37a8d35487ecbd9e21
Source dataset
uspto-grants-2006_09
Patent number
US07102007B2

Reaction notes

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