Sodium Chloride → HCID 9947001, compound

HRID 1017543Notes

Reaction equation

HRID 1017543 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[CH2:11][CH2:12][C:13]3([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:3]1=2.Cl[CH2:20][C:21]1[CH:22]=[C:23]([O:27][CH3:28])[CH:24]=[CH:25][CH:26]=1.[Cl-].[Na+]>C(N(CC)CC)C>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([CH2:20][N:16]2[CH2:17][CH2:18][C:13]3([C:3]4[N:2]([CH3:1])[C:10]5[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=5[C:4]=4[CH2:11][CH2:12]3)[CH2:14][CH2:15]2)[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 699943-Methoxybenzyl chlorideHCID 9856183HCID 9856183, compound

Product 1

HCID 9947001HCID 9947001, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 1,4-dihydro4-methylspiro[cyclopent[b]indole-3(2H), 4′-piperidine] (2.5 g) and triethylamine (2.9 ml) in dichloromethanc (100 ml) and 3-(chloromethyl)anisole (1.95 g) was stirred overnight at ambient temperature, under nitrogen. Saturated sodium chloride solution was added and the mixture was extracted with dichloromethane. The extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was flashed chromatographed (silica gel), eluting with 10% anhydrous acetone/dichloromethane. The appropriate fractions were collected and concentrated to give 1.3 g (35%) of product, mp 100-101° C.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was flashed chromatographed (silica gel)
  6. washeluting with 10% anhydrous acetone/dichloromethane
  7. customThe appropriate fractions were collected
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-af73b2a514ae45cc941dc4ac466bfb59
Source dataset
uspto-grants-2002_11
Patent number
US06479501B2

Reaction notes

Loading…