Hydrochloric Acid → N-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-N'-methyl-ethane-1,2-diamine

HRID 2103348Notes

Reaction equation

HRID 2103348 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH2:10][NH:11][CH:12]1[C:21]2[C:16](=[CH:17][C:18]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[CH:19][CH:20]=2)[CH2:15][CH2:14][CH2:13]1)C)(C)(C)C.Cl>O1CCCC1.CCOCC>[C:25]1([S:22]([C:18]2[CH:17]=[C:16]3[C:21](=[CH:20][CH:19]=2)[CH:12]([NH:11][CH2:10][CH2:9][NH:7][CH3:6])[CH2:13][CH2:14][CH2:15]3)(=[O:23])=[O:24])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57804253[2-(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-ylamino)-ethyl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 11523041N-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-N'-methyl-ethane-1,2-diamineYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

[2-(6-Benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-ylamino)-ethyl]-methyl-carbamic acid tert-butyl ester (0.4 g, 0.9 mmol) was dissolved in 20 mL of tetrahydrofuran, and 20 mL of 10% HCl in Et2O was added. The reaction mixture was refluxed for one hour and then cooled. The solvent was evaporated under reduced pressure, and the resulting solid was recrystallized from EtOH-Et2O to yield 0.3 g (0.87 mmol, 97%) of N-(6-benzenesulfonyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-N′-methyl-ethane-1,2-diamine as a hydrochloride salt. MS: 345 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for one hour
  2. temperaturecooled
  3. customThe solvent was evaporated under reduced pressure
  4. customthe resulting solid was recrystallized from EtOH-Et2O

Sources & evidence

ORD record
ord-63fca4eb8c8a49d49282f6213f684e74
Source dataset
uspto-grants-2009_08
Patent number
US07576103B2

Reaction notes

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