Benzylamine → HCID 18007303, compound

HRID 274043Notes

Reaction equation

HRID 274043 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][C:10](=O)[CH2:11][C:5]=2[CH:4]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([BH3-])#N.[Na+].[OH-].[Na+]>O.C([BH3-])#N.[Na+].C(O)(=O)C>[CH2:15]([NH:22][CH:10]1[CH2:9][CH2:8][CH2:7][C:6]2[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:11]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 7504Benzylamine2×HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 1055957491495-63-5

Product 1

HCID 18007303HCID 18007303, compound

Reagents, catalysts & solvents 3

HCID 5003444Sodium cyanoborohydrideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a mixture of 3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one (3.6 g), benzylamine (2.5 ml), and acetic acid (27 ml) in water bath was added portionwise sodium cyanoborohydride (0.49 g), and the mixture was stirred at ambient temperature for 5 hours. Additional benzylamine (2.5 ml) and sodium cyanoborohydride (0.10 g) were added to the mixture, and stirring was continued for an additional 2 hours. The reaction mixture was made alkaline (pH>8) with 10% sodium hydroxide (150 ml), and extracted once with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (gradient elution; n-hexane-ethyl acetate; 3:1 to 2:1 to 1:1) to give N-benzyl-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-amine (4.8 g) as an oil.

Workup

  1. stirringstirring
  2. waitwas continued for an additional 2 hours
  3. extractionextracted once with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (gradient elution; n-hexane-ethyl acetate; 3:1 to 2:1 to 1:1)

Sources & evidence

ORD record
ord-0906f7099905489692a4cce3391e5e4a
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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