Sodium Carbonate → N-[(1-n butyl-4-piperidyl)methyl] 2-(4-chlorobutoxy)indole-3-carboxamide

HRID 1458611Notes

Reaction equation

HRID 1458611 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][NH:12][C:13]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[O:14])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[Cl:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29].ClN1C(=O)CCC1=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][NH:12][C:13]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]=2[O:29][CH2:28][CH2:27][CH2:26][CH2:25][Cl:24])=[O:14])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 135694-Chloro-1-butanolHCID 31398ChlorosuccinimideHCID 10591304N-[(1-n butyl-4-piperidyl)methyl] indole-3-carboxamide

Product 1

HCID 10502197N-[(1-n butyl-4-piperidyl)methyl] 2-(4-chlorobutoxy)indole-3-carboxamideYield 50%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred suspension of N-[(l-n butyl-4-piperidyl)methyl] indole-3-carboxamide (Description 1b, 1.0 g, 0.0032 mole) in chloroform (25 ml) was treated with 4-chlorobutanol (0.69 ml, 0.0064 mole) followed by N-chlorosuccinimide (470 mg, 0.0035 mole) and a yellow solution was produced inside 5 minutes. After a further 40 minutes the solution was observed to darken in colour to orange. The mixture was kept at room temperature for a further 1 h then treated with 10% Na2CO3 solution (30 ml) and extracted with chloroform (2×30 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to afford an orange oil, which was chromatographed on silica gel eluting with 5% methanol/chloroform to give N-[(1-n butyl-4-piperidyl)methyl] 2-(4-chlorobutoxy)indole-3-carboxamide (0.67 g, 50%) as a yellow oil.

Workup

  1. customa yellow solution was produced inside 5 minutes
  2. waitThe mixture was kept at room temperature for a further 1 h
  3. extractionextracted with chloroform (2×30 ml)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto afford an orange oil, which
  7. customwas chromatographed on silica gel eluting with 5% methanol/chloroform

Sources & evidence

ORD record
ord-c0b0591d219a41db87803f103668d32d
Source dataset
uspto-grants-1998_12
Patent number
US05852014

Reaction notes

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