Hydrochloric Acid → m-(TRIMETHYLACETOXY)-alpha-[(METHYLAMINO)METHYL]BENZYL ALCOHOL HYDROCHLORIDE

HRID 1658764Notes

Reaction equation

HRID 1658764 reaction equation
C[C:2]1(C)[N:6](C)[CH2:5][C@@H:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH:9]=2)[O:3]1.[ClH:22].Cl.C(O)C1C=CC=CC=1>CCOCC>[ClH:22].[CH3:17][C:16]([CH3:19])([CH3:18])[C:15]([O:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH:4]([OH:3])[CH2:5][NH:6][CH3:2])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12303423(R)-2,2,3-trimethyl-5-(m-trimethylacetoxyphenyl)-1,3-oxazolidineHCID 21271294Benzyl alcohol hydrochloride

Product 1

HCID 70602254m-(TRIMETHYLACETOXY)-alpha-[(METHYLAMINO)METHYL]BENZYL ALCOHOL HYDROCHLORIDEYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The filtrate obtained in the previous reaction containing (R)-2,2,3-trimethyl-5-(m-trimethylacetoxyphenyl)-1,3-oxazolidine (1.8 g, 6.2 mmole) in 60 ml of ether was treated with hydrogen chloride gas until the solution was no longer turbid. This mixture was then evaporated to dryness and the residue was dissolved in a small amount of ethanol and then diluted with hexane. The hydrolysis and crystallization took place in the solution to give 1.2 g of the final product, (R)-m-(trimethylacetoxy)-α-[methylamino)methyl]benzyl alcohol hydrochloride, 70% yield. mp 128°-130° C, αD25° = -36.7° (C2H5OH). ir (KBr): 3370, 2690, 2795, 2420, 1750, 1610, 1590, 1460, 1240 and 1110 cm-1. nmr (CD3COCD3. D2O): δ7.5-6.8 (m, 4H), 5.3 (dd, 1H, J = 5 and 10Hz), 3.8 (b, 3H), 3.4 (m, 2H), 2.9 (s, 3H) and 1.4 (s, 9H) ppm.

Workup

  1. customThe filtrate obtained in the previous reaction
  2. customThis mixture was then evaporated to dryness
  3. dissolutionthe residue was dissolved in a small amount of ethanol
  4. additiondiluted with hexane
  5. customThe hydrolysis and crystallization

Sources & evidence

ORD record
ord-ec15a77315e0458ab957dc6a462f5ed6
Source dataset
uspto-grants-1976_06
Patent number
US03966749

Reaction notes

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