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

HRID 236843Notes

Reaction equation

HRID 236843 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.CC(C)(C)C(OC1C=C(C=CC=1)[C@@H](O)CNC)=O>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 12303424HCID 12303424, compound

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, 2960, 2795, 2420, 1750, 1610, 1590, 1460, 1240 and 1110 cm-1. nmr (CD3COCD3.D2O): δ 7.5-6.8 (m, 4H), 5.3 (dd, 1H, J=5 and 10 Hz), 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-6336716b02414145ab2a07e58f52f099
Source dataset
uspto-grants-1979_06
Patent number
US04158005

Reaction notes

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