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Methyl Bromide → N-(2-hydroxypropyl)-N,N-dimethyl-N-[3-(12-hydroxyoctadecyl)-2-hydroxypropyl]ammonium bromide

HRID 1107
Notes
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Reaction equation

HRID 1107 reaction equation
CN(CC(O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([OH:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])CCO.[CH2:29](OCCCCCCCCCCCC(O)CCCCCC)C1OC1.CNCCO.CO[CH2:60][CH:61]([OH:68])[CH2:62][N:63]([CH2:65][CH2:66][OH:67])[CH3:64].C[Br:70]>C(OCC)C>[Br-:70].[OH:68][CH:61]([CH3:60])[CH2:62][N+:63]([CH3:64])([CH3:29])[CH2:65][CH:66]([OH:67])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([OH:27])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 6323Methyl BromideHCID 80162-(Methylamino)ethanolHCID 196945981-[N-Methyl-N-(2-hydroxyethyl)amino]-3-(12-hydroxyoctadecyl)-2-propanolHCID 19694612N-(3-methoxy-2-hydroxy-propyl)-N-methyl-2-hydroxyethylamineHCID 1969465312-Hydroxyoctadecyl glycidyl ether

Product 1

HCID 19694603
N-(2-hydroxypropyl)-N,N-dimethyl-N-[3-(12-hydroxyoctadecyl)-2-hydroxypropyl]ammonium bromide
Yield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-[N-Methyl-N-(2-hydroxyethyl)amino]-3-(12-hydroxyoctadecyl)-2-propanol was first prepared from 12-hydroxyoctadecyl glycidyl ether and N-methylethanolamine in the same manner as in the preparation of N-(3-methoxy-2-hydroxy-propyl)-N-methyl-2-hydroxyethylamine in Preparation Example 24. A 200-ml autoclave was charged with 6.3 g (15 mmol) of the thus-prepared compound, 100 ml of diethyl ether and 14.2 g of methyl bromide, and the resultant mixture was stirred at 48° C. for 8 hours. The reaction mixture was then concentrated under reduced pressure, and the resultant residue was dissolved in methanol. Diethyl ether was added to the solution to form crystals. The crystals were collected by filtration, thereby obtaining 6.9 g (yield: 90%) of the title compound (IIb-4).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. dissolutionthe resultant residue was dissolved in methanol
  3. additionDiethyl ether was added to the solution
  4. customto form crystals
  5. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-540e2d8dfa8f4e3c817851023a8dc240
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723497

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes