Hydrochloric Acid → HCID 87196922, compound

HRID 337609Notes

Reaction equation

HRID 337609 reaction equation
C([O:5][C:6](=O)[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH:20]=[O:21])=[CH:12]1)(C)(C)C.Cl.[CH2:24](N(CC)CC)C.C(Cl)(=O)C>ClCCl>[CH:20]([C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]([CH2:10][CH2:9][CH2:8][NH:7][C:6](=[O:5])[CH3:24])[CH:12]=1)=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 131732019HCID 131732019, compound

Product 1

HCID 87196922HCID 87196922, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred dichloromethane (0.09 M) solution of tert-butyl[3-(3-formyl-1H-indol-1-yl)propyl]carbamate from the previous step was added HCl (4 N solution in dioxane, 45 eq.). The resulting solution was stirred at RT for 1 h before the volatiles were removed in vacuo. Dichloromethane was then added to the red residue and the volatiles were again removed in vacuo to afford a red gum. To the crude amine thus obtained was then added dichloromethane (0.09 M) and triethylamine (2.2 eq.). When the reaction solution became homogeneous, acetyl chloride (1.05 eq.) was added and the resulting mixture was allowed to stir at RT for another 2 h. The reaction was finally quenched with 1 N aq. NaOH and extracted with dichloromethane. The combined organic extracts were dried over MgSO4, filtered and concentration of the filtrate in vacuo afforded the crude title compound as a yellow solid.

Workup

  1. customwere removed in vacuo
  2. additionDichloromethane was then added to the red residue
  3. customthe volatiles were again removed in vacuo
  4. customto afford a red gum
  5. customTo the crude amine thus obtained
  6. stirringto stir at RT for another 2 h
  7. customThe reaction was finally quenched with 1 N aq. NaOH
  8. extractionextracted with dichloromethane
  9. dry with materialThe combined organic extracts were dried over MgSO4
  10. filtrationfiltered

Sources & evidence

ORD record
ord-d24e520e07524b158201ffae2e1fbba5
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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