Sodium Hydroxide → HCID 18430928, compound

HRID 1278620Notes

Reaction equation

HRID 1278620 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2([CH2:21][NH2:22])[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28].[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][C:16]2([CH2:21][NH:22][C:27](=[O:28])[CH2:26][CH2:25][CH2:24][Cl:23])[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 783704-Chlorobutyryl chlorideHCID 18430864HCID 18430864, compound

Product 1

HCID 18430928HCID 18430928, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [1-[2-(4-benzyl-1-piperazinyl)ethyl]cyclopentyl]methylamine (675 mg, 2.32 mmol) and 4-chlorobutanoylchloride (491 mg, 3.48 mmol) in tetrahydrofuran (3.48 ml) and aqueous 2 N NaOH (1.74 ml) was stirred at ambient temperature for 15 hours. The organic layers were extracted with dichloromethane (10 ml), washed with brine (4 ml) and dried over magnesium sulfate filtered and concentrated in vacuo. The residue was purified by column chromatography (NH2 gel, 230-400 mesh/30 g/hexane:ethyl acetate=1:1) to give a yellow oil (684 mg/75%).

Workup

  1. extractionThe organic layers were extracted with dichloromethane (10 ml)
  2. washwashed with brine (4 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (NH2 gel, 230-400 mesh/30 g/hexane:ethyl acetate=1:1)
  7. customto give a yellow oil (684 mg/75%)

Sources & evidence

ORD record
ord-5e2cbc36c84f4ab193ac5820d930347f
Source dataset
uspto-grants-2002_09
Patent number
US06444677B2

Reaction notes

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