Hydrochloric Acid → HCID 22321610, compound

HRID 496620Notes

Reaction equation

HRID 496620 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]#[N:23])[CH:17]=2)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.Cl.[OH-].[NH4+]>CO>[C:22]([C:18]1[CH:17]=[C:16]([CH2:15][CH2:14][N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:21]=[CH:20][N:19]=1)#[N:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 22321763HCID 22321763, compound

Product 1

HCID 22321610HCID 22321610, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

1-Boc-4-[2-(2-cyanopyridin-4-yl)ethyl]piperazine (4.0 g, 12.64 mmol) was dissolved in methanol (60 mL) and cooled to 0° C. Concentrated hydrochloric acid (10.4 mL, 126 mmol) was added and the mixture stirred for 1 h. The solvents were removed under vacuum and co-evaporated twice with methanol, a 1:1 mixture of methanol/toluene, and finally with methanol. The residue was dried under vacuum overnight to provide crude product (4.5 g). Half of the product was dissolved in methanol, concentrated ammonium hydroxide was added, and solvents were removed under vacuum. The residue was purified by chromatography (SiO2, 100:10:1 CH2Cl2:methanol:concentrated ammonium hydroxide) to provide 1-[2-(2-cyanopyridin-4-yl)ethyl]piperazine (1.05 g, 69%).

Workup

  1. customThe solvents were removed under vacuum
  2. additiona 1:1 mixture of methanol/toluene
  3. customThe residue was dried under vacuum overnight
  4. customto provide crude product (4.5 g)
  5. customsolvents were removed under vacuum
  6. customThe residue was purified by chromatography (SiO2, 100:10:1 CH2Cl2:methanol:concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-7c9cd9a116d946c482e4b32b8b7ca7ff
Source dataset
uspto-grants-2005_09
Patent number
US06946467B2

Reaction notes

Loading…