Hydrazine hydrate (1:1) → HCID 86597166, compound

HRID 1716168Notes

Reaction equation

HRID 1716168 reaction equation
[CH2:1]([O:15][CH:16]([CH2:29][O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:17]N1C(=O)C2=CC=CC=C2C1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].O.[NH2:46]N>C(O)C>[CH2:31]([O:30][CH:29]([NH2:46])[CH:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:17])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 10984952HCID 10984952, compound

Product 1

HCID 86597166HCID 86597166, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Crude N-(2,3-dimyristyloxypropyl) phthalimide 4 (20.0 g, 25.0 mmol) was dissolved in ethanol (300 ml). Hydrazine monohydrate (20 ml, 412.3 mmol) was added and the reaction was left to reflux overnight. The ethanol was removed on the rotary evaporator and the residue was redissolved in chloroform (200 ml). The precipitate was filtered off and the chloroform was removed on the rotary evaporator. TLC (10% MeOH—CHCl3, developed in Molybdate) indicated that most of the starting material had reacted to form product. This resulting product was further purified by flash column chromatography (0-5% MeOH—CHCl3) to yield 10.4 g (89.7% over three steps from 1,2-dimyristyloxypropan-3-ol 2) of 1,2-dimyristyloxypropylamine 5.

Workup

  1. waitthe reaction was left
  2. temperatureto reflux overnight
  3. customThe ethanol was removed on the rotary evaporator
  4. dissolutionthe residue was redissolved in chloroform (200 ml)
  5. filtrationThe precipitate was filtered off
  6. customthe chloroform was removed on the rotary evaporator
  7. customhad reacted
  8. customto form product
  9. customThis resulting product was further purified by flash column chromatography (0-5% MeOH—CHCl3)

Sources & evidence

ORD record
ord-952582a7e8da43ff9af0b3d7f334ead9
Source dataset
uspto-grants-2010_09
Patent number
US07803397B2

Reaction notes

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