Triethylamine → HCID 14459857, compound

HRID 1032701Notes

Reaction equation

HRID 1032701 reaction equation
Cl.Cl.CN([N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)C.[CH2:12]([N:14](CC)[CH2:15]C)C.[CH3:19][N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([C:29]([OH:31])=O)=[CH:21]1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH3:12][N:14]([CH3:15])[CH:10]1[CH2:9][CH2:8][CH2:7][N:6]([C:29]([C:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:20]([CH3:19])[CH:21]=2)=[O:31])[CH2:11]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 8540401-Methylindole-3-carboxylic acidHCID 22164878HCID 22164878, compound

Product 1

HCID 14459857HCID 14459857, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3 dimethylaminopiperidine dihydrochloride (18 g; 0.01 mol), triethylamine (2.5 g) and dichloromethane (50 ml) was stirred for 15 min. 1-Methylindole-3-carboxylic acid (2.1 g, 0.012 mol) was then added, followed by dicyclohexylcarbodiimide (2 5 g). The mixture was stirred for 48h, filtered and extracted with 1M hydrochloric acid (20+10+10 ml). The acid extracts were basified with ammonia and back extracted to chloroform. The chloroform extract was dried, evaporated and the residue dissolved in IPA (25 ml), then acidified with ethanolic hydrogen chloride to precipitate the hydrochloride 2.55 g, mp 250-251° C.

Workup

  1. filtrationfiltered
  2. extractionextracted with 1M hydrochloric acid (20+10+10 ml)
  3. extractionback extracted to chloroform
  4. extractionThe chloroform extract
  5. customwas dried
  6. customevaporated
  7. dissolutionthe residue dissolved in IPA (25 ml)
  8. customto precipitate the hydrochloride 2.55 g, mp 250-251° C.

Sources & evidence

ORD record
ord-9084c38b777046fb9baa33a631098ae5
Source dataset
uspto-grants-1990_09
Patent number
US04959375

Reaction notes

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