Dichloromethane → 5-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester

HRID 49509Notes

Reaction equation

HRID 49509 reaction equation
[CH2:1]([N:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH2:15][CH2:14]2)[CH3:5])[CH:2]=[CH2:3].C(Cl)Cl.Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)=[O:25]>>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([O:26][C:24]([N:16]2[C:17]3[C:13](=[CH:12][C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][N:4]([CH2:1][CH:2]=[CH2:3])[CH3:5])=[CH:19][CH:18]=3)[CH2:14][CH2:15]2)=[O:25])=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 1390594-Chlorophenyl chloroformateHCID 21966638Allyl-[5-(2,3-dihydro-1H-indol-5-yl)-pentyl]-methyl-amine

Product 1

HCID 102951985-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl esterYield 77.5%

Procedure

To 130 mg (0.5 mmol) Allyl-[5-(2,3-dihydro-1H-indol-5-yl)-pentyl]-methyl-amine in 2 ml CH2Cl2 0.34 ml (2 mmol) Huenig's base were added, followed by 0.28 ml (2 mmol) 4-chlorophenyl chloroformate. The solution was stirred at RT for 30 min, was concentrated and dissolved in 0.1 M NaOH and ether. The inorganic phase was extracted with ether. The combined organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with CH2Cl2/MeOH 9:1 yielded 160 mg (77%) 5-[5-(Allyl-methyl-amino)-pentyl]-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester as light yellow oil, MS: 413 (MH+, 1Cl).

Workup

  1. concentrationwas concentrated
  2. dissolutiondissolved in 0.1 M NaOH
  3. extractionThe inorganic phase was extracted with ether
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-48be4b18bf5d4b4db06dea3490d82e24
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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