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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1031587Generated: October 31, 2026

Hydrogen Bromide → (1R,4R)-6-benzyl-3,6-diazabicyclo[2.2.1]heptane dihydrobromide

https://huagongshe.com/reaction/1031587

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrogen BromideHCID 260—
Reactant(1R,4R)-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo[2.2.1]heptaneHCID 14612539—
SolventAcetic AcidHCID 176—
Product(1R,4R)-6-benzyl-3,6-diazabicyclo[2.2.1]heptane dihydrobromideHCID 1461254189%

Reaction Steps

To a hot solution of 2.85 L of hydrobromic acid 33% in acetic acid* at 70° C. there was added 1428 g (4.17 moles) of (1R, 4R)-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo-[2.2.1]-heptane (8). The solution was stirred for 12 h. The resulting suspension was cooled (18°-20° C.). The precipitate was filtered, washed with diisopropylether and dried at 40° C. under reduced pressure to give 1294 g (89%) of the titled compound. M.P. =276° C. [α]D =-0.38° (c=1, H2O).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04954507
Source datasetuspto-grants-1990_09
ORD IDord-cc3d641c58ff497dbf65aeb380c5097b
Source noteuspto-grants-1990_09