Isopropylamine → HCID 86006115, compound
Reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:7]([CH:9]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][O:11][C:12](Cl)=[O:13])[CH3:8].S(OC)(O[CH3:23])(=O)=O>C1COCC1.O>[CH2:7]([CH:9]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:10][O:11][C:12](=[O:13])[N:4]([CH:1]([CH3:3])[CH3:2])[CH3:23])[CH3:8]Participants
Conditions
- Temperature
- 40 °C
Procedure
A solution of isopropylamine (2.95 g, 50 mmol, 1 equiv.) was added at RT to a suspension of NaH (55% in mineral oil, 2.40 g, 55 mmol, 1.1 equiv.) in THF (25 ml). The mixture was warmed to 40° C. for 18 h, then chloroformic acid 2-ethyl-hexyl ester in THF (25 ml) was added dropwise over 30 min. After 4 h further stirring a suspension of NaH (55% in mineral oil, 2.40 g, 55 mmol, 1.1 equiv.) in THF (25 ml) was added followed by a solution of dimethyl sulfate (5.2 ml, 55 mmol, 1.1 equiv.) in THF (20 ml). The mixture was heated to 70° C. for 16 h, then hydrolysed by addition of water (50 ml). The hydrolysed mixture was further heated to 70° C. for 1.5 h in order to destroy excess dimethyl sulfate, then diluted with MTBE and worked up as described in Example 1. The crude product was distilled at 0.06 mbar/94-95° C. to yield 8.8 g (77%) of product.
Workup
- additionwas added
- temperatureThe mixture was heated to 70° C. for 16 h
- temperatureThe hydrolysed mixture was further heated to 70° C. for 1.5 h in order
- customto destroy excess dimethyl sulfate
- additiondiluted with MTBE
- distillationThe crude product was distilled at 0.06 mbar/94-95° C.
Sources & evidence
- ORD record
- ord-cea54f1b33f8445498270f20033e6072
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222200B2
Reaction notes
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