Isopropylamine → N-Isopropylisobutyramide

HRID 1855617Notes

Reaction equation

[C:1]([NH:5][C:6](=[O:11])[C:7](C)([CH3:9])[CH3:8])(C)([CH3:3])[CH3:2].C(N)(C)C.C(N(CC)CC)C.C(Cl)(=O)C(C)C>>[CH:1]([NH:5][C:6](=[O:11])[CH:7]([CH3:9])[CH3:8])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 6363Isopropylamine

HCID 8471Triethylamine

HCID 62325Isobutyryl chloride

HCID 299326N-tert-Butylpivalamide

Product 1

HCID 230354N-IsopropylisobutyramideYield 94%

Procedure

In a fashion similar to the preparation of LtBu,tBuH, treatment of isopropylamine (9.0 mL, 105 mmol) and triethylamine (14.9 mL, 105 mmol) with isobutyryl chloride (10.8 mL, 100 mmol) afforded LiPr,iPrH as white crystalline solid (12.14 g, 94%) upon sublimation at 55° C./0.05 Torr: mp 104-106° C.

Sources & evidence

ORD record: ord-adb50df66f5f4401908e751f353a65f6
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962876B2

Reaction notes

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