Dimethylamine → HCID 13179835, compound

HRID 543705Notes

Reaction equation

HRID 543705 reaction equation
[CH2:1]=O.[CH3:3][NH:4][CH3:5].[CH2:6]([N:13]1[CH2:18][CH2:17][CH2:16][CH:15]([C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH:21]=[CH:22][NH:23]3)[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+]>C(O)(=O)C.O>[CH3:3][N:4]([CH3:1])[CH2:5][C:21]1[C:20]2[C:24](=[CH:25][CH:26]=[CH:27][C:19]=2[CH:15]2[CH2:16][CH2:17][CH2:18][N:13]([CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:14]2)[NH:23][CH:22]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 13179834HCID 13179834, compound

Product 1

HCID 13179835HCID 13179835, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

2.5 ml of acetic acid and then 1.4 ml of an aqueous 40% formaldehyde solution were slowly added with stirring at 0° to 5° C. under an inert atmosphere to 2.5 ml of an aqueous 35% dimethylamine solution and then a solution of 5.5 g of 4-(1-benzyl-piperidin-3-yl)-1H-indole in 25 ml of acetic acid was added to the mixture. The mixture was stirred at room temperature for 90 minutes and was then diluted with water. Sodium hydroxide was added to the mixture to make it basic and the mixture was filtered. The recovered product was washed with water, dried under reduced pressure and crystallized from benzene to obtain 3 g of N,N-dimethyl-4-(1-benzyl-piperidin-3-yl)-1H-indole-3-methanamine melting at ≃150° C.

Workup

  1. filtrationthe mixture was filtered
  2. washThe recovered product was washed with water
  3. customdried under reduced pressure
  4. customcrystallized from benzene

Sources & evidence

ORD record
ord-b72d16f19c834caa8bade6fa193f4455
Source dataset
uspto-grants-1984_05
Patent number
US04447438

Reaction notes

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