Benzyl Alcohol → benzyl 1H-indole-6-carboxylate

HRID 322085Notes

Reaction equation

HRID 322085 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH2:13](O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:30]([OH:32])=[O:31])[CH:28]=2)[CH:23]=[CH:22]1.Cl>ClCCl>[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:30]([O:32][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:31])[CH:28]=2)[CH:23]=[CH:22]1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 5952301H-indole-6-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22009945benzyl 1H-indole-6-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5 g, 26.1 mmol) was added to a stirred solution of benzyl alcohol (2.47 ml, 23.9 mmol), 1H-indole-6-carboxylic acid (3.5 g, 21.7 mmol) and N,N-dimethylaminopyridine (3.4 g, 28.3 mmol) in dichloromethane (40 ml) at room temperature under a nitrogen atmosphere. After 12 h the reaction mixture was poured into 1M hydrochloric acid (200 ml) and extracted with dichloromethane (2×200 ml). The combined organics were dried (MgSO4) and concentrated to give a brown oil. Flash column chromatography (elution with dichloromethane) gave the subtitle compound (5.4 g).

Workup

  1. extractionextracted with dichloromethane (2×200 ml)
  2. dry with materialThe combined organics were dried (MgSO4)
  3. concentrationconcentrated
  4. customto give a brown oil
  5. washFlash column chromatography (elution with dichloromethane)

Sources & evidence

ORD record
ord-1d40f84d69804a468d41e77d86452ece
Source dataset
uspto-grants-2001_04
Patent number
US06211223B1

Reaction notes

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