Hydrochloric Acid → N-[6-(2-Acetylaminoethylamino)-2-phenylpyrimidin-4-yl]-2-[4-(3-chlorophenoxy)-piperidin-1-yl]-acetamide dihydrochloride

HRID 895470Notes

Reaction equation

HRID 895470 reaction equation
[ClH:1].O1CCOCC1.[C:8]([NH:11][CH2:12][CH2:13][NH:14][C:15]1[N:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:18]=[C:17]([NH:27][C:28](=[O:44])[CH2:29][N:30]2[CH2:35][CH2:34][CH:33]([O:36][C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=3)[CH2:32][CH2:31]2)[CH:16]=1)(=[O:10])[CH3:9]>CO>[ClH:43].[ClH:1].[C:8]([NH:11][CH2:12][CH2:13][NH:14][C:15]1[N:20]=[C:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:18]=[C:17]([NH:27][C:28](=[O:44])[CH2:29][N:30]2[CH2:31][CH2:32][CH:33]([O:36][C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([Cl:43])[CH:38]=3)[CH2:34][CH2:35]2)[CH:16]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 11455234N-[6-(2-Acetylaminoethylamino)-2-phenylpyrimidin-4-yl]-2-[4-(3-chlorophenoxy)-piperidin-1-yl]-acetamide

Product 1

HCID 22379221N-[6-(2-Acetylaminoethylamino)-2-phenylpyrimidin-4-yl]-2-[4-(3-chlorophenoxy)-piperidin-1-yl]-acetamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Hydrogen chloride in dioxane (4 M; 6.5 mL; 26 mmol) was added to a solution of free base 8.5 (3.38 g; 6.46 mmol) in methanol (34 mL). The slightly turbid solution was filtered through a plug of glass wool and the glassware rinsed with methanol (2×5 mL). Anhydrous ether was carefully added until a persistent precipitate just formed (56 mL). After 1 h at room temperature the flask was put into a refrigerator overnight. The white precipitate was collected on a Buchner funnel and rinsed with 4:1 ether:methanol (30 mL), 9:1 ether:methanol (30 mL) and ether (50 mL). Product was obtained as a white solid (2.88 g; 75%), mp. 195° C. (decomp.). ESIMS 522.9/524.9 (80/28) [MH+], 262.0 (50), 198.0 (100). 1H NMR (D2O) δ 8.14 (m, 2H), 7.83-7.62 (m, 4H), 7.40 (m, 1H), 7.22-7.01 (m, 3H), 4.87 (m, 1H), 4.43 (s, 2H), 3.82-3.46 (m, 8H), 2.31 (m, 4H), 1.94 (s, 3H). UV (MeOH): λmax/nm (log ε)=237 (4.72), 205 (4.78).

Workup

  1. filtrationThe slightly turbid solution was filtered through a plug of glass wool
  2. washthe glassware rinsed with methanol (2×5 mL)
  3. additionAnhydrous ether was carefully added until a persistent precipitate
  4. customjust formed (56 mL)
  5. customThe white precipitate was collected on a Buchner funnel
  6. washrinsed with 4:1 ether
  7. customProduct was obtained as a white solid (2.88 g; 75%), mp. 195° C. (decomp.)

Sources & evidence

ORD record
ord-5b4092cb757b4163a5e45383e96d25ff
Source dataset
uspto-grants-2005_07
Patent number
US06916804B2

Reaction notes

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