Ammonia → HCID 67445776, compound

HRID 472775Notes

Reaction equation

HRID 472775 reaction equation
C[O:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][C:8]([C:10]3[CH2:16][CH:15]4[NH:17][CH:12]([CH2:13][CH2:14]4)[CH:11]=3)=[CH:9][C:5]=2[CH:4]=1.O.N.[Cl:22]CCl>>[ClH:22].[CH:12]12[NH:17][CH:15]([CH2:14][CH2:13]1)[CH2:16][C:10]([C:8]1[S:7][C:6]3[CH:18]=[CH:19][C:3]([OH:2])=[CH:4][C:5]=3[CH:9]=1)=[CH:11]2

Participants

5

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 6344DichloromethaneHCID 46208386HCID 46208386, compound

Product 1

HCID 67445776HCID 67445776, compound

Procedure

3-(5-Methoxy-benzo[b]thiophen-2-yl)-8-aza-bicyclo[3.2.1]oct-2-ene (0.30 g, 1.105 mmol) was solved in dichloromethane (25 ml) and was cooled on an ice-bath. Borontribromide (1 M, 2.21 ml, 2.21 mmol) was added dropwise under cooling, followed by stirring for 15 hours at room-temperature. Water (40 ml) was added and the mixture was made alkaline by adding aqueous ammonia. The product was filtered and was recrystallised with ethanol (25 ml, 96%) and HCl in ethanol (0.5 ml, 3 M). Yield 0.15 g (46%).

Workup

  1. temperaturewas cooled on an ice-bath
  2. additionBorontribromide (1 M, 2.21 ml, 2.21 mmol) was added dropwise
  3. temperatureunder cooling
  4. filtrationThe product was filtered
  5. customwas recrystallised with ethanol (25 ml, 96%) and HCl in ethanol (0.5 ml, 3 M)

Sources & evidence

ORD record
ord-933ccd9e8b38413da961db2fa67f53f2
Source dataset
uspto-grants-2014_01
Patent number
US08633218B2

Reaction notes

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