Tryptamine → HCID 201178, compound

HRID 1637881Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O.C(O)(C(F)(F)F)=O>>[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]1[C:5]2[NH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]=2[CH2:3][CH2:2][NH:1]1

Participants

Reactant 3

HCID 1150Tryptamine

HCID 6422Trifluoroacetic acid

HCID 69962-Chlorobenzaldehyde

Product 1

HCID 201178HCID 201178, compoundYield 69%

Procedure

This product was prepared using the same procedure as for Intermediate 1 with tryptamine (1.0 g, 6.2 mmol), 2-chlorobenzaldehyde (0.7 mL, 1.0 equiv.) and TFA (1.0 mL, 2 equiv.) to give the title compound (1.2 g, 69%). 1H NMR (CDCl3) δ 7.6 (s, 1H), 7.45 (d, 1H), 7.40 (d, 1H), 6.9-7.2 (m, 6H), 5.6 (s, 1H), 3.2-3.0 (m, 2H), 2.9-2.7 (m, 2H), 2.4 (s, 1H).

Workup

customThis product was prepared

Sources & evidence

ORD record: ord-d92818c512704b2387ef91d872e0ab28
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06043252

Reaction notes

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