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Sulfuric acid magnesium salt (1:1) → {2-[2-(3,5-Dimethyl-phenyl)-1H-indol-3-yl]-ethyl}-(5-pyridin-4-yl-pentyl)-amine

HRID 1458335
Notes
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Reaction equation

HRID 1458335 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH2:20])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[N:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30][CH:31]=O)=[CH:23][CH:22]=1.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH:20][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][C:24]2[CH:23]=[CH:22][N:21]=[CH:26][CH:25]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 129045425-Pyridin-4-ylpentanalHCID 221009192-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethylamine

Product 1

HCID 9909560{2-[2-(3,5-Dimethyl-phenyl)-1H-indol-3-yl]-ethyl}-(5-pyridin-4-yl-pentyl)-amineYield 68.2%

Reagents, catalysts & solvents

1
HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]-ethylamine (162 mg) and 5-(4-pyridyl)-pentanal (100 mg in 2 mL dry chloroform) was added anhydrous magnesium sulfate (735 mg) and the mixture stirred at 0° C. for 15 minutes. At this time sodium borohydride (92.7 mg) was added followed by 3 mL dry methanol and the mixture stirred at 0° C. After 1 hour, the reaction was quenched by pouring into water (25 mL), stirred for 30 minutes then extracted with methylene chloride (4×25 mL). The combined organics were dried over potassium carbonate, concentrated in vacuo and the residue purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5) to give the title compound (172 mg). m/e=412 (M+H)

Workup

  1. stirringthe mixture stirred at 0° C
  2. waitAfter 1 hour
  3. customthe reaction was quenched
  4. additionby pouring into water (25 mL)
  5. stirringstirred for 30 minutes
  6. extractionthen extracted with methylene chloride (4×25 mL)
  7. dry with materialThe combined organics were dried over potassium carbonate
  8. concentrationconcentrated in vacuo
  9. customthe residue purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5)

Sources & evidence

ORD record
ord-bb357b7959924e24ab886736425886d0
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05849764

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes