Sodium Chloride → HCID 10109186, compound

HRID 1292464Notes

Reaction equation

HRID 1292464 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.C(N(CC)CC)C.Cl[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1.[Cl-].[Na+]>ClCCl>[CH3:35][O:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][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:29][CH:30]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 699934-Methyloxybenzyl chlorideHCID 9856183HCID 9856183, compound

Product 1

HCID 10109186HCID 10109186, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,4-dihydro-4-methylspiro[cyclopent[b]indole-3(2H),4'-piperidine] (2.5 g) and triethylamine (2.9 ml) in dichloromethane (100 ml) and 4-(chloromethyl)anisole (1.95 g) was allowed to stand overnight at ambient temperature, under nitrogen, with stirring. Saturated sodium chloride solution was added and the mixture was extracted with dichloromethane. The layers were separated, and the organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was flash chromatographed (silica gel), eluting with 7.5% acetone/dichloromethane. The appropriate fractions were collected and concentrated to give 1.5 g (40%) of product, mp 39°-40° C.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. customThe layers were separated
  3. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customchromatographed (silica gel)
  7. washeluting with 7.5% acetone/dichloromethane
  8. customThe appropriate fractions were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c536aacf273d4492b2ae0b487282d07e
Source dataset
uspto-grants-1998_05
Patent number
US05756743

Reaction notes

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