Dimethylformamide → 6-[4-(Allyl-methyl-amino)-butoxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester

HRID 49470Notes

Reaction equation

HRID 49470 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH2:22][CH2:23][CH2:24][CH2:25]Br)=[CH:18][CH:19]=3)[CH2:14][CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.[CH2:27]([CH2:30][NH2:31])[CH:28]=C.[CH3:32]N(C=O)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][N:31]([CH2:30][CH:27]=[CH2:28])[CH3:32])=[CH:18][CH:19]=3)[CH2:14][CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 4437323-Buten-1-amineHCID 695151676-(4-Bromo-butoxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester

Product 1

HCID 695152296-[4-(Allyl-methyl-amino)-butoxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl esterYield 66%

Procedure

240 mg (0.55 mmol) 6-(4-Bromo-butoxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester and 260 μl (2.7 mmol) N-allylmethylamine were stirred in 5 ml DMF at RT for 3 h. The mixture was extracted with ether and water, the organic phase was washed with water and dried over Na2SO4. Purification by column chromatography on silica gel with CH2Cl2/MeOH 9:1 yielded 154 mg (66%) 6-[4-(Allyl-methyl-amino)-butoxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester as colorless oil, MS: 429 (MH+, 1Cl).

Workup

  1. extractionThe mixture was extracted with ether and water
  2. washthe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. customPurification by column chromatography on silica gel with CH2Cl2/MeOH 9:1

Sources & evidence

ORD record
ord-f7ed43387ae348bbb36a075adb6ffc4b
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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