p-Toluenesulfonic acid → 2-(Morpholin-4-yl)methyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane

HRID 77337Notes

Reaction equation

HRID 77337 reaction equation
O[CH2:2][CH:3]1[CH2:7][O:6][C:5]2([CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:9][CH2:8]2)[O:4]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>C1(C)C=CC=CC=1>[N:32]1([CH2:2][CH:3]2[CH2:7][O:6][C:5]3([CH2:8][CH2:9][N:10]([CH2:13][CH2:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:11][CH2:12]3)[O:4]2)[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 667015182-Hydroxymethyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane

Product 1

HCID 706564532-(Morpholin-4-yl)methyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-hydroxymethyl-8-phenethyl-1,4-dioxa-8-azaspiro[4,5]decane (Compound 1.50 gm, 0.18 mole), Para Toluenesulfonic Acid (PTSA, 3.5 gms) was dissolved in toluene (300 ml) at 28° C. To this was added 18.5 gm of morpholine drop wise with continuous stirring, continued the stirring for 13 hrs at reflux temperature. Toluene was distilled under vacuum to get a semi-solid with brick red color. The yield of the product was 90%.

Workup

  1. customstirring for 13 hrs
  2. temperatureat reflux temperature
  3. distillationToluene was distilled under vacuum
  4. customto get a semi-solid with brick red color

Sources & evidence

ORD record
ord-4414bb4f86ae4421ad6735ac5301fd31
Source dataset
uspto-grants-2014_09
Patent number
US08841296B2

Reaction notes

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