Thionyl Chloride → HCID 86660688, compound

HRID 2368784Notes

Reaction equation

HRID 2368784 reaction equation
O=S(Cl)[Cl:3].[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([C@@H:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([OH:23])=O)=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:8][CH2:7]1>>[ClH:3].[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([C@@H:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([Cl:3])=[O:23])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:8][CH2:7]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 67457963HCID 67457963, compound

Product 1

HCID 86660688HCID 86660688, compoundYield 100%

Procedure

SOCl2 (2.5 L) was added to a 5 L three-neck flask. (1S)-1-(4-Methylpiperazin-1-yl)-2,3-dihydro-1H-indene-5-carboxylic acid (1289 g, the actual maximum content of 583 g, equivalent to 2.235 mol) was then added in batches within 1 hour. The solution was heated under reflux overnight and then cooled to room temperature. Most of SOCl2 was removed using rotary evaporator. After ethyl acetate (1.5 L) was added, the solution was cooled to 0° C., filtered with suction to obtain the white solid which was then dried in vacuum to get the title compound (about 1325 g, 100% yield).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux overnight
  3. customMost of SOCl2 was removed
  4. customevaporator
  5. additionAfter ethyl acetate (1.5 L) was added
  6. temperaturethe solution was cooled to 0° C.
  7. filtrationfiltered with suction
  8. customto obtain the white solid which
  9. customwas then dried in vacuum

Sources & evidence

ORD record
ord-e042d6be687b4f4d87dbe1269f994340
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Reaction notes

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