Sodium hydride → HCID 19082966, compound

HRID 1654410Notes

Reaction equation

HRID 1654410 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 19082966HCID 19082966, compound

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. After 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. concentrationAfter concentration
  7. customthe residue is crystallized in ether
  8. filtrationThe crystals are filtered
  9. washwashed with ether

Sources & evidence

ORD record
ord-0eaa1d6cad374175ad3c36fd565e0949
Source dataset
uspto-grants-1995_04
Patent number
US05405854

Reaction notes

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