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

HRID 1896816Notes

Reaction equation

HRID 1896816 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-64a153b7a9584570b2cb65abf8f15771
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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