Dimethylamine → HCID 13062398, compound
Reaction equation
[O:1]1[CH2:5][CH2:4][O:3][C:2]21[CH2:11][CH2:10][CH:9]1[CH:7]([O:8]1)[CH2:6]2.[CH3:12][NH:13][CH3:14].[OH-].[Na+]>>[CH3:12][N:13]([CH3:14])[C@H:7]1[C@H:9]([OH:8])[CH2:10][CH2:11][C:2]2([O:3][CH2:4][CH2:5][O:1]2)[CH2:6]1Participants
Procedure
A mixture of 25.0 g (0.16 mol) of spiro[7-oxabicyclo[4.1.0]-heptane-3,2'-[1,3]-dioxolane] from Example 1, Part D, and 87.0 ml (0.05 mol) of of 40% aqueous dimethylamine was heated in an oil bath at 90° for four hours. The reaction mixture was cooled to 0° and treated with NaOH pellets until two phases separated. Methylene chloride (CH2Cl2) was added, the phases were separated, the aqueous phase was extracted twice with CH2Cl2, the combined organic phases were dried (MgSO4) and the solvent removed in vacuo leaving 31.0 g of a yellow liquid. The crude yellow liquid product thus obtained was distilled at reduced pressure through a short path to give 28.0 g (88%) of the subtitled amino-alcohol: bp 83°-87° (0.2 mm); IR (nujol) 3460 (OH) cm-1, 2780 (N--C--H), 1134, 1090, 1050, 1040, 925 (C-O); mass spec. m/e 201 (M+). nmr (CDCl3); 54.7 (S, 1H, OH), 3.95 (S, 4H, O(CH2CH2O), 3.1-3.5 (m, 1H, CH-OH), δ2.3-2.7 (m, 1H, CH--N), 2.25 (S, 6H, N(CH3)2)2, 1-2 (m, 6H, ring CH2). The IR and nmr spectra were in agreement with the structure assignment.
Workup
- temperaturewas heated in an oil bath at 90° for four hours
- temperatureThe reaction mixture was cooled to 0°
- customseparated
- additionMethylene chloride (CH2Cl2) was added
- customthe phases were separated
- extractionthe aqueous phase was extracted twice with CH2Cl2
- dry with materialthe combined organic phases were dried (MgSO4)
- customthe solvent removed in vacuo
Sources & evidence
- ORD record
- ord-0b885bba09144b6daf4c6a3ce4eb07fc
- Source dataset
- uspto-grants-1982_11
- Patent number
- US04360531
Reaction notes
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