Potassium Carbonate → HCID 18436777, compound

HRID 456470Notes

Reaction equation

HRID 456470 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[OH:20])[CH2:10][CH2:9]1)(OC(C)(C)C)=O.Cl.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25]Cl.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C.O>[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 11543684Tert-butyl 4-(2-hydroxyphenyl)piperazine-1-carboxylateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 18436777HCID 18436777, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-Boc-4(2-hydroxyphenyl)-piperazine (300 mg, 1.08 mmol), 2-dimethylaminoethyl chloride hydrochloride (233 mg, 1.62 mmol), K2CO3 (450 mg, 3.26 mmol), and KI (357 mg, 2.15 mmol) in DMF (10 mL) was added 18-crown-6 (1.42 g, 5.37 mmol). After stirring overnight, water was added and the solution extracted with CH2Cl2 (3×). The combined organic extracts were concentrated to an oil. The oil was loaded onto a 10 g SCX ion exchange column equilibrated with MeOH. The column was flushed with 20 mL of MeOH, 20 mL of 0.2 M NH3 in MeOH, and 20 mL of 2 M NH3 in MeOH. The fractions containing desired product were combined and concentrated to an oil. To a solution of the oil in MeOH (2 mL) was added 1M HCl (6 mL) in Et2O. After stirring overnight the solution was concentrated to an oil to obtain the final compound. MS: 250.2 (M+1).

Workup

  1. extractionthe solution extracted with CH2Cl2 (3×)
  2. concentrationThe combined organic extracts were concentrated to an oil
  3. customThe column was flushed with 20 mL of MeOH, 20 mL of 0.2 M NH3 in MeOH, and 20 mL of 2 M NH3 in MeOH
  4. additionThe fractions containing desired product
  5. concentrationconcentrated to an oil
  6. additionTo a solution of the oil in MeOH (2 mL) was added 1M HCl (6 mL) in Et2O
  7. stirringAfter stirring overnight the solution
  8. concentrationwas concentrated to an oil

Sources & evidence

ORD record
ord-926f270de18449a19619ea6b28c964ed
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

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