Ammonia → HCID 67403453, compound

HRID 910207Notes

Reaction equation

HRID 910207 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH:14]=1)[CH:7]=[CH:6]2.N.[Cl:22]CCl>>[ClH:22].[N:15]12[CH2:16][CH2:17][CH:18]([CH2:19][CH2:20]1)[C:13]([C:8]1[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=1)[CH:4]=[C:3]([OH:2])[CH:12]=[CH:11]3)=[CH:14]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6344Dichloromethane2×HCID 115507183-(6-Methoxy-2-naphthalenyl)-1-azabicyclo[2.2.2]oct-2-ene

Product 1

HCID 67403453HCID 67403453, compound

Conditions

Temperature
-10 °C

Procedure

A mixture of 3-(6-methoxy-naphthalen-2-yl)-1-aza-bicyclo[2.2.2]oct-2-ene (0.80 g, 2.10 mmol) and dichloromethane (25 ml) was cooled to −10° C. Borontribromide (10 eq) solved in dichloromethane (21.0 ml, 21.0 mmol) was added dropwise at −10° C. The mixture was allowed to stir for 48 h. Concentrated ammonia (20 ml) was added. The phases were separated and the aqueous phase was extracted with dichloromethane (2×20 ml). The combined organic phase was dried and evaporated. The free base of the title compound was precipitated to the hydrochloric acid salt by addition of hydrogen chloride solved in ethanol. Yield 20 mg (3%). Mp 227-230° C.

Workup

  1. additionwas added dropwise at −10° C
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane (2×20 ml)
  4. customThe combined organic phase was dried
  5. customevaporated
  6. customThe free base of the title compound was precipitated to the hydrochloric acid salt by addition of hydrogen chloride

Sources & evidence

ORD record
ord-1ac8d7fd258d4f29bf0bba018360ef85
Source dataset
uspto-grants-2011_09
Patent number
US08022081B2

Reaction notes

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