Hydrochloric Acid → HCID 86740001, compound

HRID 2164799Notes

Reaction equation

HRID 2164799 reaction equation
COC1C=CC([CH:9]2[C:14]3[C:15]4[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=4[O:17][C:13]=3[CH:12]=[CH:11][N:10]2[CH3:22])=CC=1.C[S-].[Li+].Cl>CN(C)P(N(C)C)(N(C)C)=O.O>[OH:17][C:16]1[CH:18]=[CH:19][C:20]([C@@:13]23[O:17][C:16]4[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=4[C@@H:14]2[CH2:9][N:10]([CH3:22])[CH2:11][CH2:12]3)=[CH:21][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11018798HCID 11018798, compoundHCID 86740002HCID 86740002, compound

Product 1

HCID 86740001HCID 86740001, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 3.46 g of cis-1,2,3,4,4a,9b-hexahydro-4a-(4-methoxyphenyl-2-methyl-benzofuro[3,2-c]pyridine and 3.57 g of lithium thiomethoxide in 30 ml of dry hexamethylphosphoramide was heated under a drying tube at 140° for 41/2 hours. The reaction mixture was diluted with 350 ml of water, and the pH was adjusted to 7 by slow addition of 2N HCl with stirring. As the pH reached neutral, the product precipitated out. The mixture was cooled to 0° and stirred for 30 minutes. The precipitated material was filtered, washed with water and then with a small amount of ether, and dried to give 2.77 g (84.2%) of crystalline solid, m.p. s 209°, 215°-217°. Recrystallization from ethanol afforded 2.33 g (70.8%) of crystals, m.p. s 215°, 222°-224°.

Workup

  1. temperaturewas heated under a drying tube at 140° for 41/2 hours
  2. customthe product precipitated out
  3. temperatureThe mixture was cooled to 0°
  4. stirringstirred for 30 minutes
  5. filtrationThe precipitated material was filtered
  6. washwashed with water
  7. dry with materialwith a small amount of ether, and dried

Sources & evidence

ORD record
ord-b40543c820284433942f6ee91089587b
Source dataset
uspto-grants-1985_03
Patent number
US04507306

Reaction notes

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