5-Chlorovaleryl chloride → HCID 86612800, compound

A solution of [3,3-bis(ethyloxy)propyl]amine (9.02 g, 61 mmol) and diisopropylethylamine (13.3 mL, 76.4 mmol) in CH2Cl2 (50 mL) was added dropwise to a cooled (0° C.) solution of 5-chloropentanoyl chloride (10.35 g, 61 mmol) in CH2Cl2 (50 mL) over 2 h. After addition was complete the mixture was treated with 1N NaHSO4 (75 mL) and separated the layers in a separatory funnel. Back extracted the aqueous with CH2Cl2 then combined the organics, washed them with brine, dried them over MgSO4, filtered, and concentrated in vacuo. The resulting oil was chromatographed on silica gel using a gradient between 50 and 100% EtOAC in Hexanes over 100 min. Collected, combined, and concentrated in vacuo pure fractions to provide the desired product as a yellow viscous oil: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.10 (t, J=7.09 Hz, 6 H), 1.44-1.55 (m, 2 H), 1.59-1.75 (m, 4 H), 2.04 (t, J=7.23 Hz, 2 H), 3.01-3.08 (m, 2 H), 3.41 (dq, J=9.55, 7.07 Hz, 2 H), 3.50-3.64 (m, 4 H), 4.48 (t, J=5.69 Hz, 1 H), 7.74 (t, J=4.98 Hz, 1 H); ES+ MS: 288 (M+Na+).

1. additionAfter addition
2. customseparated the layers in a separatory funnel
3. extractionBack extracted the aqueous with CH2Cl2
4. washwashed them with brine
5. dry with materialdried them over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe resulting oil was chromatographed on silica gel using a gradient between 50 and 100% EtOAC in Hexanes over 100 min
9. customCollected
10. concentrationconcentrated in vacuo pure fractions

ORD record

ord-5d5c14bb53f9406eaf2933c97e90917b

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691991B2