Acetyl chloride → (R)-N-(6-(2,9-Diazaspiro[5.5]undecane-2-carbonyl)-2,3-dihydro-1H-inden-1-yl)-2-chlorobenzamide hydrochloride

HRID 1253748Notes

Reaction equation

HRID 1253748 reaction equation
C([Cl:4])(=O)C.[Cl:5][C:6]1[CH:43]=[CH:42][CH:41]=[CH:40][C:7]=1[C:8]([NH:10][C@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([N:22]3[CH2:27][CH2:26][CH2:25][C:24]4([CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]4)[CH2:23]3)=[O:21])[CH:18]=2)[CH2:13][CH2:12]1)=[O:9]>C(O)C>[ClH:4].[CH2:23]1[C:24]2([CH2:28][CH2:29][NH:30][CH2:31][CH2:32]2)[CH2:25][CH2:26][CH2:27][N:22]1[C:20]([C:17]1[CH:18]=[C:19]2[C:14]([CH2:13][CH2:12][C@H:11]2[NH:10][C:8](=[O:9])[C:7]2[CH:40]=[CH:41][CH:42]=[CH:43][C:6]=2[Cl:5])=[CH:15][CH:16]=1)=[O:21]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 59505373(R)-tert-Butyl 2-(3-(2-chlorobenzamido)-2,3-dihydro-1H-indene-5-carbonyl)-2,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 66701068(R)-N-(6-(2,9-Diazaspiro[5.5]undecane-2-carbonyl)-2,3-dihydro-1H-inden-1-yl)-2-chlorobenzamide hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetyl chloride (5 eq.) was added to an ice-cold solution of (R)-tert-butyl 2-(3-(2-chlorobenzamido)-2,3-dihydro-1H-indene-5-carbonyl)-2,9-diazaspiro[5.5]undecane-9-carboxylate (0.652 mmol, 1 eq.) in ethanol. The reaction mixture was then stirred at room temperature overnight. The solvent was concentrated in vacuo and the residue was dissolved in ethanol/acetone (1:3, 5 ml) and diethyl ether (100 ml) was added. The white solid was filtered out, washed with diethyl ether and dried in vacuo. Yield: 82%

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethanol/acetone (1:3, 5 ml)
  3. additiondiethyl ether (100 ml) was added
  4. filtrationThe white solid was filtered out
  5. washwashed with diethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e44bd6ad609b4151931b59570f51079f
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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