Propargyl bromide → HCID 22630128, compound

HRID 2307080Notes

Reaction equation

HRID 2307080 reaction equation
N1CCCCC1.[ClH:7].[CH2:8]([C:11]1([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:16][C:15]([CH3:18])([CH3:17])[CH2:14][C:13]([CH3:20])([CH3:19])[CH2:12]1)[CH:9]=[CH2:10].BrCC#C>>[ClH:7].[CH3:17][C:15]1([CH3:18])[CH2:14][C:13]([CH3:19])([CH3:20])[CH2:12][C:11]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)([CH2:8][C:9]#[CH:10])[CH2:16]1

Participants

4

Reactant 3

HCID 7842Propargyl bromideHCID 8082PiperidineHCID 22630142HCID 22630142, compound

Product 1

HCID 22630128HCID 22630128, compoundYield 6%

Procedure

Prepared from piperidine 12 according to the procedure for compound 13 (Example 5, b) using 3-bromopropyne instead of allylbromide. Yield: 6%. 1H NMR (CDCl3, TMS): 1.07 (6H, s, 3′,5′-CH3eq), 1.11 (6H, s, 3′,5′-CH3ax); 1.23 and 1.44 (total 2H, both d, 14.3 Hz, 4′-CH2); 1.75-2.00 (4H, m, piperidine 3,5-CH, 4-CH2,); 1.91 (2H, d, 13.2 Hz, 2′,6′-CHax); 2.28 (1H, s, HCC); 2.34 (2H, d, 13.2 Hz, 2′,6′-CHeq); 2.40-2.70 (2H, m, piperidine 3,5-CH); 2.81 (2H, s, CH2CC); 2.85-3.10 (2H, m, piperidine 2,6-CH); 3.69 (2H, d, 10.2 Hz, piperidine 2,6-CH) and 11.12 ppm (1H, br s, NH).

Sources & evidence

ORD record
ord-dd9701dabf81480fb0f08fbf6ae93189
Source dataset
uspto-grants-2004_12
Patent number
US06828462B2

Reaction notes

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