Benzaldehyde → Methyl 1-(4-(3-(1-admantanyl)-4-methoxybenzyloxy)benzyl)azetidine-3-carboxylate

HRID 717678Notes

Reaction equation

HRID 717678 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:24]=[CH:25][C:26]=3[O:27][CH3:28])[CH2:14][O:15][C:16]3[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:29][N:30]1CCC(=C2C3N=CC=CC=3CCC3C=CC=CC2=3)C[CH2:31]1.[CH:51](=O)C1C=CC=CC=1.Cl.N([CH2:62][C:63]([OH:65])=[O:64])C>>[C:1]12([C:11]3[CH:12]=[C:13]([CH:24]=[CH:25][C:26]=3[O:27][CH3:28])[CH2:14][O:15][C:16]3[CH:23]=[CH:22][C:19]([CH2:20][N:30]4[CH2:31][CH:62]([C:63]([O:65][CH3:51])=[O:64])[CH2:29]4)=[CH:18][CH:17]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 19861AzatadineHCID 69483Glycine, N-methyl-, hydrochloride (1:1)HCID 900025224-(3-(1-Admantanyl)-4-methoxybenzyloxy)benzaldehyde

Product 1

HCID 66615154Methyl 1-(4-(3-(1-admantanyl)-4-methoxybenzyloxy)benzyl)azetidine-3-carboxylateYield 69%

Procedure

When the product of Step B and azatadine 3 methylcarboxylate hydrochloride were substituted for 4-(5-(((4-fluorophenyl))-isopropyl)amino)methyl)thiophen-2-yl)benzaldehyde and sarcosine hydrochloride, respectively, in Example 22, Step C, the similar procedure afforded the title compound in 69% yield, as a pale paste. 1H-NMR (CDCl3) 7.24-7.20 (m, 2H); 7.16 (d, 2H, J=8.55 Hz); 6.91 (d, 2H, J=8.62 Hz); 6.85 (d, 1H, J=8.17 Hz); 4.92 (s, 2H); 3.82 (s, 3H); 3.69 (s, 3H); 3.52 (s, 2H); 3.49 (s, 1H); 3.47 (s, 2H); 3.31-3.24 (m, 3H); 2.08 (s, 6H); 2.04 (s, 3H); 1.75 (s, 6H).

Sources & evidence

ORD record
ord-b55a0717d5204ee7b0d16d87980fc4d4
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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