Water → 5-Bromo-2-(2-pyrrolidin-1-ylethoxy)benzylamine

HRID 734849Notes

Reaction equation

HRID 734849 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C:24]1[CH:37]=[C:36]([Br:38])[CH:35]=[CH:34][C:25]=1[O:26][CH2:27][CH2:28][N:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1)=[N+]=[N-].O>C1COCC1>[Br:38][C:36]1[CH:35]=[CH:34][C:25]([O:26][CH2:27][CH2:28][N:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)=[C:24]([CH:37]=1)[CH2:23][NH2:20]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 860769251-[2-(2-Azidomethyl-4-bromophenoxy)ethyl]pyrrolidine

Product 1

HCID 608783045-Bromo-2-(2-pyrrolidin-1-ylethoxy)benzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.66 g (2.50 mmol) of triphenylphosphine was added to a solution of 0.40 g (1.23 mmol) 1-[2-(2-azidomethyl-4-bromophenoxy)ethyl]pyrrolidine in 5 mL of THF and the mixture was stirred for 30 minutes at RT. Water was added and the aqueous phase was exhaustively extracted with DCM. The combined organic extracts were dried over magnesium sulfate and evaporated down in vacuo. Yield: 0.185 g (50% of theoretical); C13H19BrN2O (M=299.207); calc.: molpeak (M+H)+: 299/301 (Br); found: molpeak (M+H)+: 299/301 (Br); HPLC-MS: 1.38 minutes (method A).

Workup

  1. extractionthe aqueous phase was exhaustively extracted with DCM
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. customevaporated down in vacuo
  4. custom1.38 minutes (method A)

Sources & evidence

ORD record
ord-7cb3bb0020624d43912b34a8c10b5490
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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