Sodium hydride → (3-Benzyloxy-propyl)-cyclopropyl-amine hydrochloride

HRID 963851Notes

Reaction equation

HRID 963851 reaction equation
[C:1]([NH:8][CH:9]1[CH2:11][CH2:10]1)(OC(C)(C)C)=O.[CH2:12]([O:19][CH2:20][CH2:21]CBr)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+].[Cl-:26].[NH4+]>CN(C=O)C>[ClH:26].[CH2:12]([O:19][CH2:20][CH2:21][CH2:1][NH:8][CH:9]1[CH2:10][CH2:11]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2776064Benzyl 3-Bromopropyl EtherHCID 15698228tert-Butyl N-cyclopropylcarbamate

Product 1

HCID 19082966(3-Benzyloxy-propyl)-cyclopropyl-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.58 g of N-BOC-cyclopropylamine and 15 g of O-benzyl-3-bromo-1-propanol in 90 ml of DMF are treated at 0°-5° with 2.5 g of sodium hydride (55% in oil). The mixture is stirred at 0°-5° for 1 hour and at room temperature for 3 hours and then treated at 0°-5° with aqueous ammonium chloride solution. The mixture is partitioned in ether/water and the ether phases are washed with water, then dried and concentrated. After chromatography over silica gel with ether/hexane (1:4), the 11.5 g of product are stirred with 120 ml of 4.8 molar hydrochloric acid in dioxane. Sifter concentration, the residue is crystallized in ether. The crystals are filtered and washed with ether. There are obtained 9.0 g of (3-benzyloxy-propyl)-cyclopropyl-amine hydrochloride, MS (EI): 206 (M+H).

Workup

  1. customThe mixture is partitioned in ether/water
  2. washthe ether phases are washed with water
  3. customdried
  4. concentrationconcentrated
  5. stirringAfter chromatography over silica gel with ether/hexane (1:4), the 11.5 g of product are stirred with 120 ml of 4.8 molar hydrochloric acid in dioxane
  6. concentrationSifter concentration
  7. customthe residue is crystallized in ether
  8. filtrationThe crystals are filtered
  9. washwashed with ether

Sources & evidence

ORD record
ord-b2f166c2ec2c4e27ba6cc56797bfe3e1
Source dataset
uspto-grants-1998_06
Patent number
US05763604

Reaction notes

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