Hydrochloric Acid → HCID 67356691, compound

HRID 268753Notes

Reaction equation

HRID 268753 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11][CH2:12][NH:13][CH3:14])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[ClH:21]>CCOCC.C1COCC1>[ClH:21].[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:11][CH2:12][NH:13][CH3:14])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 45273676HCID 45273676, compound

Product 1

HCID 67356691HCID 67356691, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent

Procedure

To a solution of [3-(1H-indol-5-yl)-3-phenyl-propyl]-carbamic acid methylester X (0.52 g, 1.7 mmol) in THF (35 ml), LiAlH4 (321 mg, 8.4 mmol) was slowly added. The mixture was refluxed for 1.5 hours, cooled to room temperature, and quenched by slow addition of freshly ground Na2SO4.10H2O. The mixture was stirred at room temperature for 1 hour, filtered through celite with EtOAc. The filtrate was evaporated and purified via flash chromatography (DCM/MeOH/NH4OH) affording [3-(1H-indol-5-yl)-3-phenyl-propyl]-methyl-amine (XI) as an off-white foam (408 mg, 91% yield). The amine compound was dissolved in a Et2O/THF mixture and HCl (2 M in Et2O, 0.772 ml) was added. The precipitate was filtered, washed with Et2O, and dried affording [3-(1H-indol-5-yl)-3-phenyl-propyl]-methyl-amine hydrochloride salt (371 mg, 80% yield). MS (M+H)=265.

Workup

  1. additionwas added
  2. filtrationThe precipitate was filtered
  3. washwashed with Et2O
  4. customdried

Sources & evidence

ORD record
ord-2ae2575cc40a42e8b9f1d0fda322e109
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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