Hydrochloric Acid → HCID 13450867, compound

HRID 1155101Notes

Reaction equation

HRID 1155101 reaction equation
B.[CH:2]1([C:5]([N:7]2[CH:14]3[CH2:15][N:10]([C:11]4[CH:19]=[C:18]([NH:20][C:21](=O)[CH2:22][CH2:23][CH3:24])[CH:17]=[CH:16][C:12]=4[CH2:13]3)[CH2:9][CH2:8]2)=O)[CH2:4][CH2:3]1.Cl.[OH-].[Na+]>O1CCCC1.O>[CH:2]1([CH2:5][N:7]2[CH:14]3[CH2:15][N:10]([C:11]4[CH:19]=[C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:17]=[CH:16][C:12]=4[CH2:13]3)[CH2:9][CH2:8]2)[CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 14798Sodium HydroxideHCID 13450863HCID 13450863, compound

Product 1

HCID 13450867HCID 13450867, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Borane in tetrahydrofuran (1 M, 250 ml.) was added slowly to a mixture of 4-cyclopropanecarbonyl-9-butyramido-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (the product of part A of this example) and tetrahydrofuran (200 ml.) and the resulting mixture was heated under reflux. Water was added dropwise, and the tetrahydrofuran was boiled off. The mixture was acidified with hydrochloric acid, heated on a steam bath, basified with sodium hydroxide, and extracted with chloroform. The chloroform extract was dried, filtered and concentrated to dryness. Crystallization of the resulting orange oil from hexane afforded 4-cyclopropylmethyl-9-butylamino-3,4,5,6-tetrahydro-2H-1,5-methano-1,4-benzodiazocine (4.8 g., m.r. 84°-85° C.), the compound of Formula I wherein Q is cyclopropylmethyl, R is hydrogen and R' is butyl.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux
  3. temperatureheated on a steam bath
  4. extractionextracted with chloroform
  5. extractionThe chloroform extract
  6. customwas dried
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customCrystallization of the resulting orange oil from hexane

Sources & evidence

ORD record
ord-2dff37ed1e024d0e8fb7d8c50fc2ab60
Source dataset
uspto-grants-1981_11
Patent number
US04299830

Reaction notes

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