Hydrochloric Acid → N-{3-[7-Amino-8-(4-chlorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl]propyl}propane-1-sulfonamide hydrochloride

HRID 1044518Notes

Reaction equation

HRID 1044518 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH2:18][CH2:19][NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22])[CH:15]=3)[CH2:10][CH2:9][CH:8]2[NH:27]C(=O)OC(C)(C)C)=[CH:4][CH:3]=1.Cl>ClCCl>[ClH:1].[NH2:27][CH:8]1[CH:7]([CH2:6][C:5]2[CH:35]=[CH:36][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:16]2[CH:15]=[C:14]([CH2:17][CH2:18][CH2:19][NH:20][S:21]([CH2:24][CH2:25][CH3:26])(=[O:23])=[O:22])[CH:13]=[CH:12][C:11]=2[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59547819tert-Butyl [1-(4-chlorobenzyl)-7-{3-[(propylsulfonyl)amino]propyl}-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate

Product 1

HCID 57471345N-{3-[7-Amino-8-(4-chlorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl]propyl}propane-1-sulfonamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl [1-(4-chlorobenzyl)-7-{3-[(propylsulfonyl)amino]propyl}-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate (150 mg, 0.281 mmol) was dissolved in dichloromethane (3 mL) and a solution of hydrochloric acid (0.5 mL, 5 M in isopropanol) was added. After stirring at room temperature for 2 hours the solvent was removed in vacuo. Water was added (15 mL) and the pH was adjusted to 9 with aqueous saturated sodium bicarbonate and the mixture was extracted with dichloromethane (3×15 mL). The combined organic extracts were dried and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, dichloromethane, methanol). The product was dissolved in dichloromethane (2 mL) and a solution of hydrochloric acid in ethanol (1.25 M) was added. The solvent was removed in vacuo. Yield: 31.4 mg (0.187 mmol, 36%).

Workup

  1. customwas removed in vacuo
  2. additionWater was added (15 mL)
  3. extractionthe mixture was extracted with dichloromethane (3×15 mL)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (silica gel, dichloromethane, methanol)
  7. dissolutionThe product was dissolved in dichloromethane (2 mL)
  8. additiona solution of hydrochloric acid in ethanol (1.25 M) was added
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0b450934d04f472bb3987e76dead5c12
Source dataset
uspto-grants-2013_10
Patent number
US08563617B2

Reaction notes

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