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

HRID 2212504Notes

Reaction equation

HRID 2212504 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-0dade4adfe1a4269984b9d5d391a42ca
Source dataset
uspto-grants-2006_09
Patent number
US07102007B2

Reaction notes

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