Hydrogen Bromide → (1R,4R)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide

HRID 981988Notes

Reaction equation

HRID 981988 reaction equation
[BrH:1].Br.C1(C[N:10]2[CH2:15][C@H:14]3[CH2:16][C@@H:11]2[CH2:12][NH:13]3)C=CC=CC=1.C1(C)C=CC(S(N2C[C@H]3C[C@@H]2CN3CC2C=CC=CC=2)(=O)=O)=CC=1.Br>CC(O)=O>[BrH:1].[BrH:1].[C@@H:11]12[CH2:16][C@@H:14]([NH:13][CH2:12]1)[CH2:15][NH:10]2

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14612539(1R,4R)-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo[2.2.1]heptaneHCID 14612541(1R,4R)-6-benzyl-3,6-diazabicyclo[2.2.1]heptane dihydrobromide

Product 1

HCID 14612496(1R,4R)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromideYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

(1R,4R)-5-phenylmethyl-2,5-diazabicyclo[2.2.1] heptane dihydrobromide. A mixture of (1R,4R)-2-(4-toluenesulfonyl)-5-phenylmethyl-2,5-diazabicyclo[2.2.1]heptane (38.95 g, 0.11 mole) in AcOH (500 mL) containing HBr (30% wt) was heated at 70° C. for 18 h. The mixture was allowed to cool and the precipitate that formed was filtered and washed with acetone. The filtrate was concentrated to one-third of the original volume and the resulting solid was combined with the first precipitate to give the title compound (36.55 g, 92%, m.p. 272°-275° C.).

Workup

  1. temperatureto cool
  2. customthe precipitate that formed
  3. filtrationwas filtered
  4. washwashed with acetone
  5. concentrationThe filtrate was concentrated to one-third of the original volume

Sources & evidence

ORD record
ord-0c78e1b58bc5406885308983ccc0a11e
Source dataset
uspto-grants-1991_02
Patent number
US04994460

Reaction notes

Loading…