Tert-Butylamine → n-tert-butylpropanamide

HRID 1855615Notes

Reaction equation

[C:1]([NH:5][C:6](=[O:11])[C:7](C)(C)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N)(C)(C)C.C(N(CC)CC)C.C(Cl)(=O)CC>>[C:1]([NH:5][C:6](=[O:11])[CH2:7][CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 4

HCID 6385Tert-Butylamine

HCID 8471Triethylamine

HCID 62324Propionyl chloride

HCID 299326N-tert-Butylpivalamide

Product 1

HCID 239177n-tert-butylpropanamideYield 95%

Procedure

In a fashion similar to the preparation of LtBu,tBuH, treatment of tert-butylamine (11.3 mL, 105 mmol) and triethylamine (14.9 mL, 105 mmol) with propionyl chloride (8.9 mL, 100 mmol) afforded LEt,tBuH as white crystalline solid (12.27 g, 95%) upon sublimation at 55° C./0.05 Torr: mp 90-92° C.

Sources & evidence

ORD record: ord-7743c2ad4b9a452c93861ccb22f30fd0
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962876B2

Reaction notes

Loading…