Acetyl chloride → HCID 52918896, compound

HRID 1423152Notes

Reaction equation

HRID 1423152 reaction equation
Cl.Cl.[CH2:3]([N:10]([CH3:32])[CH2:11][C@H:12]1[CH2:17][N:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:19]=2)[CH2:15][CH2:14][NH:13]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:40](Cl)(=[O:42])[CH3:41].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:3]([N:10]([CH2:11][C@H:12]1[CH2:17][N:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:19]=2)[CH2:15][CH2:14][N:13]1[C:40](=[O:42])[CH3:41])[CH3:32])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 67291888HCID 67291888, compound

Product 1

HCID 52918896HCID 52918896, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)—N-benzyl-1-(4-(3-(cyclopentyloxy)-4-methoxyphenyl)piperazin-2-yl)-N-methylmethanamine dihydrochloride, (Example 42, Compound 130) (96.5 mg, 0.20 mmol) in CH2Cl2 (2 mL) at 0-5 C was treated with triethylamine (84 ul, 0.60 mmol) followed by acetyl chloride (22 uL, 0.30 mmol). The reaction mixture was allowed to warm to room temperature and stir 1 h. After this time the reaction mixture was treated with a saturated aqueous solution of NaHCO3 (1 mL). The organic portion was then dried over MgSO4, filtered, and evaporated to afford quenched with evaporated and the residue purified by silica gel flash chromatography with 100% EtOAc then 5% MeOH/EtOAc as eluant to afford product as an oil (65 mg, 72%). LC/MS (Method B) 2.57 min, [M+1]+ 452. Potency class ND.

Workup

  1. dry with materialThe organic portion was then dried over MgSO4
  2. filtrationfiltered
  3. customevaporated
  4. customto afford
  5. customquenched
  6. customwith evaporated
  7. customthe residue purified by silica gel flash chromatography with 100% EtOAc

Sources & evidence

ORD record
ord-220047635bcf49aab4873c696af30cd8
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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