Acetic Anhydride → (S)-1-(2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)ethanone

HRID 1423116Notes

Reaction equation

HRID 1423116 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>N1C=CC=CC=1>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[C:28](=[O:30])[CH3:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 16725642(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine

Product 1

HCID 23627684(S)-1-(2-benzyl-4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-1-yl)ethanoneYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of the bis-hydrochloride salt of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine in pyridine (1 mL) was treated with acetic anhydride (32 μL, 0.34 mmol) and stirred for 16 h. The reaction mixture was evaporated and partitioned between EtOAc (2 mL) and a saturated aqueous NaHCO3 solution (2 mL). The organic component was separated, dried over MgSO4, filtered, and evaporated to residue which was purified by silica gel flash chromatography with EtOAc as eluant to afford the title compound as an oil (45 mg, 97%). LC/MS (Method A) 6.88 min, [M+1]+ 409.

Workup

  1. customThe reaction mixture was evaporated
  2. custompartitioned between EtOAc (2 mL)
  3. customThe organic component was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to residue which
  7. customwas purified by silica gel flash chromatography with EtOAc as eluant

Sources & evidence

ORD record
ord-140850a2560e4cf9b2523220ee754a55
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

Loading…