3-Chlorophenethylamine → N-[2-(3-chlorophenyl)ethyl]-N-(4-dodec-1-ynylbenzyl)amine Hydrochloride

HRID 735933Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1.[C:11]([C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([C:11]#[C:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:24][CH:25]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 1393813-Chlorophenethylamine

HCID 865985364-Dodec-1-ynylbenzaldehyde

Product 1

HCID 67188385N-[2-(3-chlorophenyl)ethyl]-N-(4-dodec-1-ynylbenzyl)amine HydrochlorideYield 50%

Procedure

The same procedure as employed in the preparation of Example 226 (step a) but using [2-(3-chlorophenyl)ethyl]amine and 4-dodec-1-ynylbenzaldehyde gave the title compound as a white powder (50%). 1H NMR (DMSO-dr, 300 MHz) δ 9.27 (br s, 1H), 7.51-7.24 (m, 8H), 4.15 (br s, 2H), 3.14 (br s, 2H), 2.98 (m, 2H), 1.99 (m, 2H), 1.55-1.40 (m, 16H), 0.85 (t, 3H, J=6.6 Hz). M−(LC/MS(ESI)): 411. HPLC (Condition A), Rt: 5.30 min (HPLC purity: 99.9%).

Workup

customThe same procedure as employed in the preparation of Example 226 (step a) but

Sources & evidence

ORD record: ord-36f29e2932664092b43a39b19b0b3403
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

Loading…