Hydrochloric Acid → Pruvanserin hydrochloride

HRID 1013056Notes

Reaction equation

HRID 1013056 reaction equation
[CH2:1]1[N:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2F)[CH2:5][CH2:4][N:3]([C:17]([C:19]2[C:24]3[NH:25][CH:26]=[C:27]([C:28]#[N:29])[C:23]=3[CH:22]=[CH:21][CH:20]=2)=[O:18])[CH2:2]1.O.[ClH:31]>CC(C)=O>[ClH:31].[F:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][N:6]2[CH2:5][CH2:4][N:3]([C:17]([C:19]3[CH:20]=[CH:21][CH:22]=[C:23]4[C:24]=3[NH:25][CH:26]=[C:27]4[C:28]#[N:29])=[O:18])[CH2:2][CH2:1]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 22017550HCID 22017550, compound

Product 1

HCID 9887933Pruvanserin hydrochlorideYield 69%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

2.1 g of the free base of EMD281014 are heated in 50 ml of acetone, and water is added until a clear solution is formed. A mixture of 0.6 ml of hydrochloric acid (w=37%) and 1.2 ml of acetone is then stirred in. The mixture is subsequently evaporated to half the volume in a rotary evaporator. The precipitated hydrochloride is filtered off with suction, washed with acetone and diethyl ether and dried, giving 1.6 g of 7-{4-[2-(4-fluorophenyl)ethyl]-piperazine-1-carbonyl}-1H-indole-3-carbonitrile, hydrochloride (69% of theory), decomposition range 314-319°.

Workup

  1. customis formed
  2. customThe mixture is subsequently evaporated to half the volume
  3. customin a rotary evaporator
  4. filtrationThe precipitated hydrochloride is filtered off with suction
  5. washwashed with acetone and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-2ca00d1822e0467c964b916007dd649f
Source dataset
uspto-grants-2011_07
Patent number
US07981897B2

Reaction notes

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