Water → Benzyl-(6-fluoroindan-1-yl)-amine

HRID 2175051Notes

Reaction equation

HRID 2175051 reaction equation
[CH2:1]([N:8]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].ClCCl.O>C(O)C>[CH2:1]([NH:8][CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=2)[CH2:11][CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 90019076Benzyl-(6-fluoroindan-1-ylidene)-amine

Product 1

HCID 90019384Benzyl-(6-fluoroindan-1-yl)-amineYield 94.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve benzyl-(6-fluoroindan-1-ylidene)-amine (23.22 g, 97.03 mmol) in ethanol (1200 mL). Cool the mixture to 0° C. under nitrogen. Add sodium borohydride (11.01 g, 291.10 mmol) to the mixture. After one hour, add dichloromethane (150 mL) and water (150 mL). Stir for 14 hours under nitrogen and concentrate in vacuo to remove ethanol. Extract the residue with dichloromethane and saturated aqueous sodium chloride. Dry the resulting organics with magnesium sulfate, filter, and concentrate in vacuo to give the title compound as a red oil (22.12 g, 94%). MS (ES) m/z=242 [M+1].

Workup

  1. concentrationconcentrate in vacuo
  2. customto remove ethanol
  3. extractionExtract the residue with dichloromethane and saturated aqueous sodium chloride
  4. dry with materialDry the resulting organics with magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-ae1aeca5d76948d39fddeb53bcfb7b0c
Source dataset
uspto-grants-2015_06
Patent number
US09062050B2

Reaction notes

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