Hydrochloric Acid → Hydrochloric Acid

HRID 353265Notes

Reaction equation

HRID 353265 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([N:18]([CH3:35])[C@@H:19]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=2)[CH2:20][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:17])=[CH:11][CH:10]=1)=O)CCC.[ClH:36].[OH-].[Na+]>C1(OC)C=CC=CC=1.CC(O)=O>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([N:18]([CH3:35])[C@@H:19]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=2)[CH2:20][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:17])=[CH:11][CH:10]=1.[ClH:36]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11306208HCID 11306208, compound

Product 2

HCID 313Hydrochloric AcidHCID 114404582-(4-Aminophenyl)-N-methyl-N-[(1S)-1-(3-nitrophenyl)-2-(1-pyrrolidinyl)ethyl]acetamide

Reagents, catalysts & solvents 2

HCID 7519AnisoleCatalystHCID 176Acetic AcidSolvent

Procedure

The product from Example 59 (2.9211 g, 6.053 mmol) and anisole (2 drops) were mixed in AcOH (10 mL) and 4N HCl (10 mL) and stirred at 25° C. overnight, fitted with a drying tube. The mixture was adjusted to pH 13 with 1N NaOH with stirring in ice-H2O and then extracted with CH2Cl2 (2×70 mL). The combined organic fraction was dried (Na2SO4), filtered through celite, and evaporated. The product was gravity column chromatographed eluting with CHCl3:2% NH3 before it was converted to the HCl salt with Et2O—HCl to yield 15 HCl.(0.5531 g, 22%, unoptimized): m.p. (HCl salt) 200° C. (dec); 1H NMR (HCl salt, DMSO-d6) δ1.98 (br s, 4H, —CH2CH2—), 2.86 (s, 3H, —NCH3), 3.2-4.3 (complex, 8H, 4 —CH2—), 7.16 (d, J=7.4 Hz, 2H, aromatic), 7.33 (d, J=7.5 Hz, 2H, aromatic), 7.7 (m, 2H, aromatic), 8.08 (s, 1H, aromatic), 8.23 (m, 1H, aromatic). MS(FAB) m/z 383. Anal. (C, H, N) C21H26N4O30.2HCl.0.75H2O.

Workup

  1. customfitted with a drying tube
  2. extractionextracted with CH2Cl2 (2×70 mL)
  3. dry with materialThe combined organic fraction was dried (Na2SO4)
  4. filtrationfiltered through celite
  5. customevaporated
  6. customchromatographed
  7. washeluting with CHCl3

Sources & evidence

ORD record
ord-bccf6b51c3124d4d9f332921f3737649
Source dataset
uspto-grants-2004_06
Patent number
US06750216B2

Reaction notes

Loading…