Hydrochloric Acid → HCID 68711170, compound

HRID 1818812Notes

Reaction equation

HRID 1818812 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([NH:26]C(=O)OC(C)(C)C)[CH2:22][CH2:21]2)[S:9]1(=[O:35])=[O:34].[ClH:36]>CCOCC.CO.CCOCC>[ClH:36].[ClH:36].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]2)[S:9]1(=[O:35])=[O:34]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86621289HCID 86621289, compound

Product 1

HCID 68711170HCID 68711170, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21864698Diethyl ether methanolSolvent

Procedure

tert-butyl (1-{3-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]propyl}piperidin-4-yl)carbamate (0.40 g, 0.80 mmol) was dissolved in ether:methanol (9:1) and 2 mL of 2N HCl in ether added. The solution was allowed to stand for 16 hr whereupon a colorless solid had formed. The solid was removed by filtration and washed with ether to afford 0.33 g (87%) 1-{3-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]propyl}piperidin-4-amine dihydrochloride. HPLC purity 98.7% at 210-370 nm, 5.5 min.; Xterra RP18, 3.5 u, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff.Ph=3.5/ACN+MeOH) for 10 min, hold 4 min. HRMS: calcd for C20H25FN4O2S+H+, 405.17550; found (ESI, [M+H]+Obs'd), 405.1768.

Workup

  1. customhad formed
  2. customThe solid was removed by filtration
  3. washwashed with ether

Sources & evidence

ORD record
ord-e1756b8f6c79434682cd8169479b2557
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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