Sodium borohydride → 4-(Pyrrolidin-1-ylmethyl)benzylamine

HRID 1191002Notes

Reaction equation

HRID 1191002 reaction equation
[N:1]1([CH2:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[N:1]1([CH2:6][C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 49628034-((Pyrrolidin-1-yl)methyl)benzonitrile

Product 1

HCID 49628544-(Pyrrolidin-1-ylmethyl)benzylamineYield 45%

Reagents, catalysts & solvents 2

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 4-(pyrrolidin-1-ylmethyl)-benzonitrile (918 mg, 4.93 mmol) in methanol (32 mL). Add cobalt(II) chloride hexahydrate (2.7 g, 9.87 mmol) and stir for 20 min. Cool the mixture to 0° C., and carefully add sodium borohydride (1.86 g, 49.3 mmol) in small batches. Stir the mixture for 1.5 h at room temperature. Quench the mixture with water and partition between water and chloroform. Extract the aqueous phase three times with chloroform/iso-propanol (3:1). Dry the combined organic extracts over MgSO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel (80 g) eluting with a gradient of DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 19:1 over 5 min, 9:1 over 5 min, 85:15; 50 mL/min) to give the title compound (421 mg, 45%). MS (ES+) m/z: 191 (M+H)+,

Workup

  1. customQuench the mixture with water
  2. custompartition between water and chloroform
  3. extractionExtract the aqueous phase three times with chloroform/iso-propanol (3:1)
  4. dry with materialDry the combined organic extracts over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify by chromatography on silica gel (80 g)
  8. washeluting with a gradient of DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 19:1 over 5 min, 9:1 over 5 min, 85:15; 50 mL/min)

Sources & evidence

ORD record
ord-39a68ce39c8443d88322682717fb2d02
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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