Hydrochloric Acid → (1S,3S)-N1,N1-dimethylcyclopentane-1,3-diamine dihydrochloride

HRID 1420312Notes

Reaction equation

HRID 1420312 reaction equation
CC(OC(=O)[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([N:13]([CH3:15])[CH3:14])[CH2:9]1)(C)C.[ClH:17]>O1CCOCC1>[ClH:17].[ClH:17].[CH3:14][N:13]([C@H:10]1[CH2:11][CH2:12][C@H:8]([NH2:7])[CH2:9]1)[CH3:15]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 67640823(1S-trans)-[3-(N,N-Dimethylamino)cyclopentyl]carbamic acid 1,1-dimethylethyl ester

Product 1

HCID 70347448(1S,3S)-N1,N1-dimethylcyclopentane-1,3-diamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent4×

Procedure

(1-S-trans)-[3-(N,N-Dimethylamino)cyclopentyl]carbamic acid 1,1-dimethylethyl ester (0.537 g, 2.35 mmol) in 1,4-dioxan (4 ml) was treated with a saturated solution of hydrogen chloride in 1,4-dioxan (15 ml) and additional 1,4-dioxan (8 ml). After 50 minutes at 21° C., another portion of a saturated solution of hydrogen chloride in 1,4-dioxan (5 ml) was added, and after a further 2.5 h, the opaque solution was concentrated by evaporation to give the title compound as a beige solid, which was used without characterisation.

Workup

  1. waitafter a further 2.5 h
  2. concentrationthe opaque solution was concentrated by evaporation

Sources & evidence

ORD record
ord-de3a063879944cb5aefd0c2ef6a9ae48
Source dataset
uspto-grants-1999_03
Patent number
US05889178

Reaction notes

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