Methyl Isobutyl Ketone → HCID 20544104, compound

HRID 2285726Notes

Reaction equation

HRID 2285726 reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13](Cl)[CH:14]=3)[NH:9][CH:8]=2)[CH2:3][CH2:2]1.C[C:18]([CH2:20][CH:21](C)C)=[O:19].C(=O)([O-])[O-].[Na+].[Na+].ClCCCO[CH:35]1[CH2:40][CH2:39][CH2:38][O:37][CH2:36]1>O>[O:37]1[CH2:36][CH2:35][CH2:40][CH2:39][CH:38]1[O:19][CH2:18][CH2:20][CH2:21][N:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 30505325-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 20544101HCID 20544101, compound

Product 1

HCID 20544104HCID 20544104, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 11.6 g of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-5-chloro-1H-indole, 120 ml of isobutyl methyl ketone, 15.9 g of sodium carbonate and 22 ml of 3-(3-chloropropyloxy)-tetrahydro-2H-pyran was stirred at 100°-105° C. under an inert atmosphere for 24 hours and was cooled and poured into 500 ml of water. The mixture was stirred for one hour and was extracted with ethyl acetate. The organic phase was washed with water and with aqueous sodium chloride solution, dried and evaporated to dryness. The 29.6 g of crystalline residue were chromatographed over silica gel and eluted with a 6-3-1 chloroform-acetone-triethylamine mixture to obtain 13.1 g of 3-[1-(3-{2-tetrahydropyranyloxy}-propyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-indole in the form of crystals melting at 161° C.

Workup

  1. temperaturewas cooled
  2. stirringThe mixture was stirred for one hour
  3. extractionwas extracted with ethyl acetate
  4. washThe organic phase was washed with water and with aqueous sodium chloride solution
  5. customdried
  6. customevaporated to dryness
  7. customThe 29.6 g of crystalline residue were chromatographed over silica gel
  8. washeluted with a 6-3-1 chloroform-acetone-triethylamine mixture

Sources & evidence

ORD record
ord-bb5108e3238e4004b3a815734b3b4b6e
Source dataset
uspto-grants-1982_04
Patent number
US04324790

Reaction notes

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