Hydrochloric Acid → 1-(Chloromethyl)cyclopentan-1-amine hydrochloride

HRID 276268Notes

Reaction equation

HRID 276268 reaction equation
[ClH:1].O[CH2:3][C:4]1([NH2:9])[CH2:8][CH2:7][CH2:6][CH2:5]1.Cl.O=S(Cl)[Cl:13]>O1CCOCC1>[ClH:13].[Cl:1][CH2:3][C:4]1([NH2:9])[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 23143728(1-Aminocyclopentyl)methanol hydrochloride

Product 1

HCID 699924851-(Chloromethyl)cyclopentan-1-amine hydrochlorideYield 100.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-hydroxymethylcyclopentanamine HCl salt (Method B1c; 20 g, 0.17 mol) in anh. p-dioxane (65 mL) was added HCl (4M in p-dioxane; 65 mL, 0.26 mol). The resulting solution was stirred for 20 min. at room temp., then SOCl2 (22.7 g, 0.19 mol) was added dropwise. The reaction mixture was heated at 80° C. for 2 d, cooled to room temp., and concentrated under reduced pressure to give 1-chloromethylcyclopentanamine HCl salt (29 g, 100%): CI-MS m/z 171 ((M+H)+).

Workup

  1. temperaturecooled to room temp.
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-009ee3455b26493ab92946bee0d9af18
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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