Triethylamine → 2-Benzyloxy-3-hexadecyloxypropyl 1,1-dimethyl-1,2,3,4-tetrahydroquinolinio-2-ylmethyl phosphate

HRID 1088566Notes

Reaction equation

HRID 1088566 reaction equation
[CH2:1]([O:8][CH:9]([CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([O-])(=O)=[O:37])=CC=1.[CH3:41][N+:42]1([CH3:54])[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH2:45][CH2:44][CH:43]1[CH2:52][OH:53].[P:55](Cl)(Cl)(Cl)=[O:56].C(N(CC)CC)C>N1C=CC=CC=1.C(Cl)(Cl)Cl>[P:55]([O-:56])([O:53][CH:52]=[C:43]1[CH2:44][CH2:45][C:46]2[C:51](=[CH:50][CH:49]=[CH:48][CH:47]=2)[N+:42]1([CH3:54])[CH3:41])([O:11][CH2:10][CH:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:37]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 132771402-(Benzyloxy)-3-(hexadecyloxy)propan-1-olHCID 150522411,1-Dimethyl-1,2,3,4-tetrahydro-2-hydroxymethylquinolinium p-toluenesulfonate

Product 1

HCID 1317166582-Benzyloxy-3-hexadecyloxypropyl 1,1-dimethyl-1,2,3,4-tetrahydroquinolinio-2-ylmethyl phosphate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

The procedures of Example 7 were repeated using 406 mg of 2-benzyloxy-3-hexadecyloxy-1-propanol, 580 mg of 1,1-dimethyl-1,2,3,4-tetrahydro-2-hydroxymethylquinolinium p-toluenesulfonate prepared in Reference Example 11, 0.1 ml of phosphorus oxychloride, 0.3 ml of triethylamine, 3 ml of chloroform having passed through an alumina column, and 8 ml of dry pyridine, to give 150 mg of the desired compound.

Sources & evidence

ORD record
ord-a8f4cde856f74174b0eb0c25705bc817
Source dataset
uspto-grants-1990_10
Patent number
US04962096

Reaction notes

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