Hydrochloric Acid → HCID 66817915, compound

HRID 1755071Notes

Reaction equation

HRID 1755071 reaction equation
Cl.C(OC(=O)NC)(C)(C)C.O1[C:15]2([CH2:20][CH2:19][N:18]([S:21]([C:24]3([CH2:27][C:28]4[C:33]([CH3:34])=[CH:32][C:31]([NH:35][CH3:36])=[CH:30][C:29]=4[CH3:37])[CH2:26][CH2:25]3)(=[O:23])=[O:22])[CH2:17][CH2:16]2)[O:14]CC1.[OH-].[Na+]>CCO>[CH3:37][C:29]1[CH:30]=[C:31]([NH:35][CH3:36])[CH:32]=[C:33]([CH3:34])[C:28]=1[CH2:27][C:24]1([S:21]([N:18]2[CH2:17][CH2:16][C:15](=[O:14])[CH2:20][CH2:19]2)(=[O:23])=[O:22])[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 527635tert-Butyl methylcarbamateHCID 66818604HCID 66818604, compound

Product 1

HCID 66817915HCID 66817915, compoundYield 286.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A 5 N aqueous HCl solution (2.0 ml, 10 mmol) was added to a solution of a mixture of 4-[1-(1,4-dioxa-8-aza-spiro[4.5]decane-8-sulfonyl)-cyclopropylmethyl]-3,5-dimethyl-phenyl}-methyl-carbamic acid tert-butyl ester (54.7 mg, 0.111 mmol) and {4-[1-(1,4-dioxa-8-aza-spiro[4.5]decane-8-sulfonyl)-cyclopropylmethyl]-3,5-dimethyl-phenyl}-methyl-amine (23.1 mg, 0.0585 mmol) in EtOH (2.0 mL), and the mixture was stirred at 80° C. for two hours. The reaction mixture was neutralized by adding a 5 N aqueous NaOH solution (1.9 ml) and then extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated under reduced pressure to give 1-[1-(2,6-dimethyl-4-methylamino-benzyl)-cyclopropanesulfonyl]-4-piperidinone (58.8 mg, 99%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0dc4dc400ed46519196fef32491944d
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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