Hydrochloric Acid → HCID 131723555, compound

HRID 991679Notes

Reaction equation

HRID 991679 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1.O(C(C)(C)C)[Na].Br[CH2:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[ClH:37]>COCCOC>[ClH:37].[O:30]([CH2:29][CH2:28][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 68526Benzene, (2-bromoethoxy)-HCID 11543684Tert-butyl 4-(2-hydroxyphenyl)piperazine-1-carboxylateHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 131723555HCID 131723555, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
55 °C

Procedure

The product from Step 1 above (0.55 g, 2.0 mmol) was added to a stirred solution of NaO-t-Bu (0.55 g, 2.0 mmol) in DME (5 mL). After 5 min, β-bromophenetole (0.56 g, 2.8 mmol) was added, and the reaction was stirred at 55° C. for 15 h. 2 M HCl was added, and the reaction mixture was stirred for another 3 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between 2 M NaOH/CHCl3. The aqueous phase was extracted with CHCl3 (×3). The combined organic layers were dried (MgSO4), concentrated, and the residue was purified by chromatography on silica gel using CHCl3/MeOH/NH4OH (90:10:0.4) as eluent to give the free base of the title compound. The free base was treated with HCl/ether, and the resulting hydrochloride salt was dried (80° C., 1 mmHg) to afford 0.254 g (35%) of the title compound as a light brown semi-solid material that solidified upon standing. Anal. (C18H22N2O2.HCl. H2O) H, N; C: calc, 61.27; found, 61.9.

Workup

  1. stirringthe reaction mixture was stirred for another 3 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between 2 M NaOH/CHCl3
  4. extractionThe aqueous phase was extracted with CHCl3 (×3)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a627dbbcc2d14820866e48da8b9d7301
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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