Hydrochloric Acid → HCID 19040651, compound

HRID 1683768Notes

Reaction equation

HRID 1683768 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[C:5]([CH:14]=[O:15])=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.[OH-].[Na+]>CO.[Cl-].[Na+].O>[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12][C:6]=2[C:5]([CH2:14][OH:15])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 19040638HCID 19040638, compound

Product 1

HCID 19040651HCID 19040651, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 9-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepine-6-carboxaldehyde (3.07 g, 13.8 mmol) in methanol (35 ml) was cooled to 5° C. and treated with sodium borohydride (3.07 g, 81 mmol). The mixture was stirred for 15 minutes at 5° C. and for 45 minutes at 25° C. The mixture was cooled and carefully treated with dilute hydrochloric acid. The mixture was diluted with brine, basified with 10% sodium hydroxide and extracted with ethyl acetate. The organic phase was dried, concentrated and the residue chromatographed on silica gel eluted with a gradient of methanol-methylene chloride (5:95-9:91) to give 1.45 g (47%) of 9-chloro-2,3,4,5-tetrahydro-3-methyl-1H-3-benzazepine-6-methanol; mp 136.5°-140° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customthe residue chromatographed on silica gel
  6. washeluted with a gradient of methanol-methylene chloride (5:95-9:91)

Sources & evidence

ORD record
ord-8655c0e950d442fcb75ed32126740ea0
Source dataset
uspto-grants-1997_06
Patent number
US05639748

Reaction notes

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