Hydrochloric Acid → HCID 178511248, compound

HRID 479275Notes

Reaction equation

HRID 479275 reaction equation
C(OC(=O)[NH:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][NH:16][S:17]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:11][CH2:10]1)(C)(C)C.Cl>C(Cl)(Cl)Cl.O1CCOCC1>[NH2:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][NH:16][S:17]([C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178453605HCID 178453605, compound

Product 1

HCID 178511248HCID 178511248, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of trans-{4-[(naphthalene-1-sulfonylamino)-methyl]-cyclohexylmethyl}-carbamic acid tert-butyl ester (25 g) in chloroform (300 ml) is treated with a 4 N HCl solution in dioxane (300 ml) at 0° C. After completion, the reaction mixture is concentrated in vacuo, the residue is taken up in a 1 N sodium hydroxide solution and dichloromethane. After extraction with dichloromethane, the organics are dried over sodium sulfate and concentrated to 18.5 g of trans-naphthalene-1-sulfonic acid (4-aminomethyl-cyclohexylmethyl)-amide as a white powder melting at 157-162° C. Rf (C3) 0.36.

Workup

  1. concentrationAfter completion, the reaction mixture is concentrated in vacuo
  2. extractionAfter extraction with dichloromethane
  3. dry with materialthe organics are dried over sodium sulfate
  4. concentrationconcentrated to 18.5 g of trans-naphthalene-1-sulfonic acid (4-aminomethyl-cyclohexylmethyl)-amide as a white powder melting at 157-162° C

Sources & evidence

ORD record
ord-02a153cabbbc46c4b6526d38aa139289
Source dataset
uspto-grants-2003_11
Patent number
US06645774B1

Reaction notes

Loading…