Hydrochloric Acid → HCID 75530025, compound

HRID 895366Notes

Reaction equation

HRID 895366 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[Cl:22])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:23]>CO>[ClH:21].[ClH:23].[Cl:22][C:16]1[C:17]([Cl:21])=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22379716HCID 22379716, compound2×

Product 1

HCID 75530025HCID 75530025, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[(tert-butyloxycarbonyl]-N′-(2,3-dichlorobenzyl)piperazine [Intermediate 3, (8.25 g, 24 mmol)] in MeOH (200 mL) was added concentrated aqueous HCl solution (15 mL) slowly in portions. The reaction was stirred overnight and the first crop of product crystallized out. The reaction mixture was filtered and the filter cake was rinsed with Et2O to afford a white crystalline solid (4.1 g). The filtrate was concentrated to about ⅓ of the original volume and a second crop of crystalline product was collected by filtration (2.9 g). The combined yield of the title product was 92%. 1H NMR (DMSO-d6) δ 9.81 (br, 2H), 7.87 (d, J=7.5 Hz, 1H), 7.75 (d, J=8.0 Hz), 7.47 (t, J=7.9 Hz), 4.45 (s, 2H), 3.40 (s, 4H), 3.16 (s, 1H); 13C NMR (DMSO-d6) δ 133.0, 132.6, 132.5, 131.9, 128.7, 56.9, 48.2, 40.6; MS Calcd for [C11H14Cl2N2+H]+: 245. found: 245.

Workup

  1. customthe first crop of product crystallized out
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake was rinsed with Et2O

Sources & evidence

ORD record
ord-ccf57e72bf9b4723969e37fc4f868edf
Source dataset
uspto-grants-2005_07
Patent number
US06916812B2

Reaction notes

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