Hydrochloric Acid → HCID 9798696, compound

HRID 1584130Notes

Reaction equation

HRID 1584130 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][NH:11]C(OC(C)(C)C)=O)[CH:5]=[CH:4][C:3]=1[NH:19][C:20](=[O:40])[C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]2)=[CH:23][CH:22]=1.Cl>CCOC(C)=O>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][NH2:11])[CH:5]=[CH:4][C:3]=1[NH:19][C:20](=[O:40])[C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15870799HCID 15870799, compound

Product 1

HCID 9798696HCID 9798696, compoundYield 120.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 200 mL round bottomed flask with a stirring bar and a gas dispersion tube was added N-(2-methyl-4-(2-(1,1-dimethylethoxycarbonylamino)ethoxy)phenyl)-4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)benzamide (0.912 g, 1.64 mmol) and 100 mL of dry EtOAc. This well stirred solution was cooled in an ice bath and saturated with HCl gas over 15 min. The mixture was aged 1 h at 0° C. and the excess HCl was then removed with a stream of argon. The EtOAc was removed in vacuo and the crude product was recrystallized from MeOH-EtOAc to give 0.70 g of N-(2-methyl-4-(2-aminoethoxy)phenyl)-4-(1-piperazinyl)benzamide, dihydrochlorlide as a white solid. mp:>250° C. 1H NMR (CD3OD): d 2.27 (s, 3H), 3.29 (m, 1H), 3.30 (m, 6H), 3.57 (m, 4H), 4.24 (t, j=5 Hz, 3H), 6.87 (dd, j=5,9 Hz, 1H), 6.94 (d, j=5 Hz, 1H), 7.12 (d, j=9 Hz, 2H), 7.22 (d, j=9 Hz, 1H), 7.91 (d, j=9Hz, 2H).

Workup

  1. customthe excess HCl was then removed with a stream of argon
  2. customThe EtOAc was removed in vacuo
  3. customthe crude product was recrystallized from MeOH-EtOAc

Sources & evidence

ORD record
ord-e1d2d563b1f04ca08320937ea53b3aa1
Source dataset
uspto-grants-1999_08
Patent number
US05932582

Reaction notes

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