Hydrochloric Acid → HCID 86618489, compound

HRID 1454233Notes

Reaction equation

HRID 1454233 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([CH:19]=[CH:20][C:21]=1[F:22])[CH2:9][N:10]1[CH2:15][CH2:14][N:13]([CH:16]([CH3:18])[CH3:17])[CH2:12][CH2:11]1.Cl>C(Cl)Cl>[F:22][C:21]1[CH:20]=[CH:19][C:8]([CH2:9][N:10]2[CH2:11][CH2:12][N:13]([CH:16]([CH3:18])[CH3:17])[CH2:14][CH2:15]2)=[CH:7][C:6]=1[CH:2]=[O:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68849724HCID 68849724, compound

Product 1

HCID 86618489HCID 86618489, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(3-[1,3] dioxolan-2-yl-4-fluoro-benzyl)-4-isopropyl-piperazine (695.2 mg, 2.25 mmol) and 6 N HCl (25 mL) was stirred at rt for 50 min, then was diluted with DCM (250 mL), and quenched slowly with 1 N NaOH. The organic layer was separated, dried (Na2SO4), and concentrated to give the desired product (573.5 mg, 96%). MS (ESI): mass calcd. for C15H21FN2O, 264.16; m/z found, 265.3 [M+H]+. 1H NMR (MeOD): 10.29 (s, 1H), 7.82-7.81 (m, 1H), 7.68-7.66 (m, 1H), 7.58-7.56 (m, 1H), 7.31-7.28 (m, 1H), 7.26-7.04 (m, 1H), 7.03-7.01 (t, J=8.4, 1H), 3.55 (s, 1H), 3.50 (s, 1H), 2.64-2.40 (br m, 9H), 1.07-1.06 (m, 6H).

Workup

  1. customquenched slowly with 1 N NaOH
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-77c1e9f7dec246e68d97f21a0caee7cd
Source dataset
uspto-grants-2009_01
Patent number
US07479493B2

Reaction notes

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