Triethylamine → HCID 15617956, compound

HRID 1194395Notes

Reaction equation

HRID 1194395 reaction equation
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:8]2[C:24](O)=[O:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-].ClC1C=CC=C[NH+]=1.C(N(CC)CC)C.[NH2:42][CH2:43][CH:44]([OH:51])[CH2:45][N:46]([CH2:49][CH3:50])[CH2:47][CH3:48]>C(Cl)Cl>[CH2:47]([N:46]([CH2:45][CH:44]([OH:51])[CH2:43][NH:42][C:24]([C:8]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:15]2[C:10]([C:9]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:25])[CH2:49][CH3:50])[CH3:48]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 977491-Amino-3-(diethylamino)propan-2-olHCID 13885791HCID 13885791, compoundHCID 14866494HCID 14866494, compound

Product 1

HCID 15617956HCID 15617956, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.5 g of N-phenyl-3-benzyloxyindole-2-carboxylic acid are reacted with 4.5 g of 2-chloro-N-pyridinium iodide, 4.2 ml of triethylamine and 2.5 g of 1-amino-2-hydroxy-3-diethylaminopropane in 45 ml of methylene chloride at room temperature, After 14 h, the reaction mixture is washed with a saturated solution of sodium chloride and with a 10% sodium carbonate solution, dried over sodium sulfate, filtered and evaporated. The residue is dissolved in dilute hydrochloric acid/ether and the ether phase separated. The aqueous phase is made alkaline and extracted with ether. The ether extract is washed with water, dried over sodium sulfate and evporated. The raw 2-[3-N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-benzyloxy-1-phenylindole is recrystallized from isopropanol/ether. Melting point: 80°-81° C.

Workup

  1. washthe reaction mixture is washed with a saturated solution of sodium chloride and with a 10% sodium carbonate solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe residue is dissolved in dilute hydrochloric acid/ether
  6. customthe ether phase separated
  7. extractionextracted with ether
  8. extractionThe ether extract
  9. washis washed with water
  10. dry with materialdried over sodium sulfate
  11. customThe raw 2-[3-N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-benzyloxy-1-phenylindole is recrystallized from isopropanol/ether

Sources & evidence

ORD record
ord-f6897f4ec3634c7890aac9a2cac950e9
Source dataset
uspto-grants-1989_03
Patent number
US04814345

Reaction notes

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