Hydrochloric Acid → 1-(4,4-Dimethoxycyclohexyl)but-3-en-1-amine

HRID 2175500Notes

Reaction equation

HRID 2175500 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]([NH:15]S(C(C)(C)C)=O)[CH2:12][CH:13]=[CH2:14])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Cl>CO>[CH3:3][O:4][C:5]1([O:1][CH3:2])[CH2:10][CH2:9][CH:8]([CH:11]([NH2:15])[CH2:12][CH:13]=[CH2:14])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58562759N-(1-(1,4-dioxaspiro[4.5]decan-8-yl)but-3-en-1-yl)-2-methylpropane-2-sulfinamide

Product 1

HCID 585627941-(4,4-Dimethoxycyclohexyl)but-3-en-1-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(1-(1,4-dioxaspiro[4.5]decan-8-yl)but-3-en-1-yl)-2-methylpropane-2-sulfinamide (828 mg, 2.63 mmol), prepared in the previous step, was dissolved in methanol (20 mL) and treated with HCl (4.4 mL. 5.5 mmol, 1.25 M in MeOH), stirring overnight at room temperature. The reaction mixture was concentrated in vacuo, triturated with ether, decanting the supernatant several times and the residue dried under high vacuum afford the product as a white foam (HCl salt).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customtriturated with ether
  3. customdecanting the supernatant several times
  4. customthe residue dried under high vacuum
  5. customafford the product as a white foam (HCl salt)

Sources & evidence

ORD record
ord-598fab4fc7ab4a5eb11dfde6a75e7c59
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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