Hydrochloric Acid → 5-Aminomethyl-2-methyl-1h-indole-3-carboxylic acid benzyl ester, hydrochloride

HRID 966535Notes

Reaction equation

HRID 966535 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][NH:21]C(OC(C)(C)C)=O)[CH:18]=2)[NH:13][C:12]=1[CH3:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:30].O1CCOCC1>C(Cl)Cl>[ClH:30].[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][NH2:21])[CH:18]=2)[NH:13][C:12]=1[CH3:29])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 102940355-(tert-Butoxycarbonylamino-methyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

Product 1

HCID 1317251805-Aminomethyl-2-methyl-1h-indole-3-carboxylic acid benzyl ester, hydrochlorideYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(tert-butoxycarbonylamino-methyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (1.8 g, 4.6 mmol) in methylene chloride (10 μL) was added 4 M hydrogen chloride in dioxane (1.2 mL, 4.8 mmol). The mixture was stirred at room temperature for 1 hour and the formed solid was then filtered. The product was further purified by recrystallization (ethanol and methylene chloride) to give 950 mg (63%) of titled product as a beige solid: mp 260-261° C.; MS(APCI−): m/z 293.1 (M−H); Anal. Calcd for C18H18N2O2.1.06HCl: C, 64.92; H, 5.77; N, 8.41; Cl, 11.29. Found: C, 64.58; H, 5.79; N, 8.31; Cl, 11.38.

Workup

  1. filtrationthe formed solid was then filtered
  2. customThe product was further purified by recrystallization (ethanol and methylene chloride)

Sources & evidence

ORD record
ord-4514e186169b4b82ad268f65fc536649
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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