Hydrochloric Acid → HCID 178510006, compound

HRID 1757011Notes

Reaction equation

HRID 1757011 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([NH:18][C@H:19]3[CH2:24][CH2:23][C@H:22]([C:25]([O:27]C)=[O:26])[CH2:21][CH2:20]3)=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[OH-].[Li+].Cl>O1CCCC1.O>[NH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([NH:18][C@H:19]3[CH2:24][CH2:23][C@H:22]([C:25]([OH:27])=[O:26])[CH2:21][CH2:20]3)=[O:17])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178501237HCID 178501237, compound

Product 1

HCID 178510006HCID 178510006, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

400 mg of 1-(4-aminomethylphenyl)-4-[N-[trans-4-(methoxycarbonyl)-cyclohexyl]-aminocarbonyl]-piperazine-hydrochloride and 3 ml of a 1.4 molar aqueous lithium hydroxide solution in 3 ml of tetrahydrofuran and 2 ml of water is stirred at ambient temperature for 2 hours. Then 3.2 ml of 1N hydrochloric acid are added dropwise and some of the solvent is evaporated off under reduced pressure. The precipitate is suction filtered, triturated with acetone, suction filtered again and dried. Yield: 330 mg (94% of theory), Rf value: 0.47 (silica gel; methylene chloride/methanol/conc. ammonia=2:1:0.25) Mass spectrum: M+ =360

Workup

  1. customsome of the solvent is evaporated off under reduced pressure
  2. filtrationfiltered
  3. customtriturated with acetone, suction
  4. filtrationfiltered again
  5. customdried

Sources & evidence

ORD record
ord-c907e793e9344f9a96d56fca0c7a62c1
Source dataset
uspto-grants-1995_08
Patent number
US05442064

Reaction notes

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