Hydrochloric Acid → HCID 11983234, compound

HRID 493089Notes

Reaction equation

HRID 493089 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16][C:17]1[C:18]2[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=2[O:20][CH:21]=1)C)(C)(C)C.C(OCC)C.Cl>CO>[O:20]1[CH:21]=[C:17]([S:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][NH:7][CH3:6])[C:18]2[CH:25]=[CH:24][CH:23]=[CH:22][C:19]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68896983HCID 68896983, compound

Product 1

HCID 11983234HCID 11983234, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[2-(Benzo[b]furan-3-ylsulfanyl)-benzyl]-methyl-carbamic acid tert-butyl ester (9.2 g, 24.9 mmol) is dissolved in methanol (75 mL) and diethyl ether saturated with hydrochloric acid (75 mL) is added. The mixture is stirred at ambient temperature for 1 hour and then concentrated in vacuo. Water (50 mL) is added to the remanence and the mixture is basified by addition of aqueous ammonia (conc.). The aqueous fraction is extracted with ethyl acetate (3×100 mL). The combined organic fractions are dried (MgSO4) and concentrated in vacuo. The product is purified by preparative HPLC or by silica gel chromatography eluting with ethyl acetate-triethyl amine (25:1) to furnish the title compound as an oil. This oil can be redissolved in ethyl acetate (75 mL). Diethyl ether saturated with hydrochloric acid can be added hereto until pH 2. The precipitated material can then be filtered off and dried in vacuo to give 6.9 g (91%) of [2-(benzo[b]furan-3-ylsulfanyl)-benzyl]-methyl-amine hydrochloride as a white crystalline material.

Workup

  1. concentrationconcentrated in vacuo
  2. additionWater (50 mL) is added to the remanence
  3. additionthe mixture is basified by addition of aqueous ammonia (conc.)
  4. extractionThe aqueous fraction is extracted with ethyl acetate (3×100 mL)
  5. dry with materialThe combined organic fractions are dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe product is purified by preparative HPLC or by silica gel chromatography
  8. washeluting with ethyl acetate-triethyl amine (25:1)

Sources & evidence

ORD record
ord-56f49701bd0f4070962d7f0f6f22b5e5
Source dataset
uspto-grants-2009_05
Patent number
US07534791B2

Reaction notes

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